SU677653A3 - Способ получени 2-бензоил-3аминопиридинов или их солей - Google Patents

Способ получени 2-бензоил-3аминопиридинов или их солей

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Publication number
SU677653A3
SU677653A3 SU742043816A SU2043816A SU677653A3 SU 677653 A3 SU677653 A3 SU 677653A3 SU 742043816 A SU742043816 A SU 742043816A SU 2043816 A SU2043816 A SU 2043816A SU 677653 A3 SU677653 A3 SU 677653A3
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USSR - Soviet Union
Prior art keywords
benzoyl
chloropyridine
salts
aminopyridine
producing
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SU742043816A
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English (en)
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Фон Бебенбург Вальтер
Офферманнс Хериберт
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Дегусса (Фирма)
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Publication of SU677653A3 publication Critical patent/SU677653A3/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

(54) СПОСОБ ПОЛУЧЕНИЯ 2-БЕНЗОИЛ-ЗАМИНОПИРИДИНОВ ИЛИ ИХ СОЛЕЙ
Реакцию алкилировани  провод т при добавке обычных св зывающих кислоту оснований , таких как щелочные карбонаты, щелочные гидриды, щелочные амиды, щелочные алкогол ты, пиридин или другие третичные амины, при температуре от О до 150°С в инертных растворител х, таких как спирты, диоксан, диметилформамид, диметилсульфоксид , ароматические углеводороды , например бензол, толуол, или ацетон.
Алкилирование может производитьс  таким образом, что сход т из соединени  формулы II, последнее сначала ацилируют, затем ввод т алкильный остаток (как указано выше, преимущественно в присутствии оснований или активных щелочных соединений ) и затем кислотный остаток гидролизуют .
Омыление возможно проводить в воде, метаноле, этаноле или в лед ной уксусной кислоте или в смес х этих или других растворителей , которые содержат соответствующую , используемую дл  гидролиза кислоту или основание (поташ, сода, щелочь, NHa и т. д.). Температура реакции лежит обычно от 20 до 150°С.
Основани  соединений общей формулы I могут переводитьс  в соли известными методами .
Из солей могут обычным способом снова получатьс  свободные основани , например обработкой раствора в таком органическом растворителе, как спирт (метанол), содой или едким натром, или разбавленными кислотами (например,разбавленной уксусной).
Те соединени  формулы I, которые содержат асимметрические атомы углерода и получаютс  как рацематы, могут расщепл тьс  известным образом, например при помощи оптически активной кислоты, на оптически активные изомеры. Но можно сразу примен ть также оптически активное исходное вещество, причем в этом случае в качестве конечного продукта получаетс  соответствующа  оптически активна  или диастереомерна  форма.
Пример 1. 2-Бензоил-3-метиламино-6хлорпиридин .
43 г 2-бензоил-3-амино-6 - хлорпиридина раствор ют в 100 мл диоксана, добавл ют 16 мл пиридина и при перемешивании 18 мл пропионилхлорида. Перемешивают в течение 2 ч и добавл ют воду до начала кристаллизации . Осажденное вещество перекристаллизовывают из метанола-воды. Выход 48 г; т. пл. 140°С.
47 г 2-бензоил-3-пропиониламино-6-хлорпиридина раствор ют в 200 мл диметилформамида , при перемешивании в атмосфере азота добавл ют 5,5 г 80%-ного гидрида натри , через 30 мин прибавл ют по капл м 29 мл йодистого метила. Смесь перемешивают 2 ч при 50°С, добавл ют 10 мл йетанола и упаривают в вакууме. Соединение получаетс  в виде масла.
50 г 2-бензоил-3-(пропионилметиламино)6-хлорпиридина раствор ют в 100 мл этанола , добавл ют 200 мл воды и 200 мл концентрированной сол ной кислоты. Смесь кип т т 10 ч, затем смешивают с одним литром воды. Масло кристаллизуетс  при растирании. Вещество перекристаллизовывают из этанола. Выход 24 г; т. нл. 77°С. Пример 2. 2-(о-Хлорбензоил)-3-метиламино-6-хлорпиридин .
134 г 2-(о-хлорбензоил)-З-амино-б-хлорпиридина суспендируют в 200 мл хлороформа и при перемешивании прибавл ют по капл м при 30-35°С ангидрид трифторуксусной кислоты. После 30 мин перемешивани  реакционную смесь упаривают досуха и остаток перекристаллизовывают из этанола . Выход 147,5 г; т. пл. 148°С.
Смесь 158 г 2-(о-хлорбензоил)-3-трифторацетиламино-6-хлорпиридина , 247 г йодистого метила и 1500 мл ацетона нагревают при перемешивании до 48°С, затем добавл ют в течение 5 мин 97,5 г мелкоизмельченное едкое кали при таком охлаждении
водой, чтобы температура не превышала 50°С. Растворитель упаривают в вакууме, остаток перемешивают с 660 мл смеси этанола-воды (10 : 1), при этом продукт реакции осаждаетс  в кристаллической форме . Продукт отфильтровывают и перекристаллизовывают из 600 мл «-пропанола. Выход 29 г; т. пл. 149°С.
Пример 3. 2-(о-Фторбензоил)-3-метиламино-6-хлорпиридин .
Смесь 68 г 2-(о-фторбензоил)-3-трифторацетиламино-6-хлорпиридина , полученного аналогично предыдзщему примеру из 50 г 2-(о-фторбензоил)-3-амино - 6-хлорпиридина , 116 г йодистого метила, 700 мл ацетона
обрабатывают, как в предыдущем примере. Выход 39 г; т. пл. 148°С. .Пример 4. 2-Бензоил-3-бутиламино-6хлорпиридин . К раствору 140 г 2-бензоил-3-амино-6хлорпиридина в 900 мл диметилформамида добавл ют при перемешивании при 30- 40°С 20 г гидрида натри  в масле (80%) и через 30 мин прибавл ют по капл м 80 мл йодистого бутила. Смесь выдерживают 5 ч
при 80-90°С, затем смешивают с 100 мл этанола и после короткого перемешивани  растворитель удал ют в вакууме. Остаток очищают на силикагеле (элюирование с хлороформом), причем требуемое соединение элюируетс  как перва  зона. Выход 30 г; вещество представл ет собой масло.

Claims (1)

1. Вейганд-Хальгетаг. Методы эксперимента в органической химии. М., «Хими , 1968, с. 413.
SU742043816A 1972-05-10 1974-07-17 Способ получени 2-бензоил-3аминопиридинов или их солей SU677653A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AT411372A AT321303B (de) 1972-05-10 1972-05-10 Verfahren zur Herstellung von neuen 2-Benzoyl-3-amino-pyridin-Verbindungen und deren Salzen

Publications (1)

Publication Number Publication Date
SU677653A3 true SU677653A3 (ru) 1979-07-30

Family

ID=3559825

Family Applications (4)

Application Number Title Priority Date Filing Date
SU1914703A SU538662A3 (ru) 1972-05-10 1973-04-26 Способ получени производных 2-бензоил-3-аминопиридина или их солей
SU742043814A SU597338A3 (ru) 1972-05-10 1974-06-17 Способ получени производных 2-бензоил-3-амино-6-галоидпиридинов или их солей
SU2043813A SU561508A3 (ru) 1972-05-10 1974-07-17 Способ получени производных 2-бензоил3-(аминоацетиламидо)-пиридина или их солей
SU742043816A SU677653A3 (ru) 1972-05-10 1974-07-17 Способ получени 2-бензоил-3аминопиридинов или их солей

Family Applications Before (3)

Application Number Title Priority Date Filing Date
SU1914703A SU538662A3 (ru) 1972-05-10 1973-04-26 Способ получени производных 2-бензоил-3-аминопиридина или их солей
SU742043814A SU597338A3 (ru) 1972-05-10 1974-06-17 Способ получени производных 2-бензоил-3-амино-6-галоидпиридинов или их солей
SU2043813A SU561508A3 (ru) 1972-05-10 1974-07-17 Способ получени производных 2-бензоил3-(аминоацетиламидо)-пиридина или их солей

Country Status (23)

Country Link
US (1) US3875176A (ru)
JP (1) JPS4948674A (ru)
AR (2) AR207633Q (ru)
AT (1) AT321303B (ru)
AU (1) AU469111B2 (ru)
BE (1) BE799339A (ru)
CA (1) CA991189A (ru)
CH (2) CH582150A5 (ru)
CS (1) CS181238B2 (ru)
DD (1) DD106378A5 (ru)
DE (1) DE2319872A1 (ru)
EG (1) EG11137A (ru)
ES (3) ES413174A1 (ru)
FR (1) FR2184077B1 (ru)
GB (1) GB1416459A (ru)
HU (1) HU169037B (ru)
IL (1) IL42007A (ru)
NL (1) NL7306170A (ru)
PL (1) PL91935B1 (ru)
RO (1) RO63441A (ru)
SE (1) SE415974B (ru)
SU (4) SU538662A3 (ru)
ZA (1) ZA732013B (ru)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4007290A (en) * 1974-01-09 1977-02-08 General Foods Corporation Caffeine antagonim
EP0032516B1 (en) * 1980-01-16 1984-05-02 Lacer, S.A. New 2-halo-pyridines, their production and pharmaceutical compositions
JPH01104580U (ru) * 1988-01-05 1989-07-14
JP2531989B2 (ja) * 1988-09-14 1996-09-04 吉富製薬株式会社 ピリジン化合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3781360A (en) * 1966-01-14 1973-12-25 Schering Corp 2-polyfluoroloweralkylamino benzophenones
US3763178A (en) * 1968-09-05 1973-10-02 American Home Prod Imidazolinyl phenyl carbonyl acid addition salts and related compounds

Also Published As

Publication number Publication date
IL42007A0 (en) 1973-06-29
NL7306170A (ru) 1973-11-13
SU597338A3 (ru) 1978-03-05
CA991189A (en) 1976-06-15
CH605761A5 (ru) 1978-10-13
AR201105A1 (es) 1975-02-14
AT321303B (de) 1975-03-25
AU5553773A (en) 1974-11-14
PL91935B1 (ru) 1977-03-31
JPS4948674A (ru) 1974-05-11
CH582150A5 (ru) 1976-11-30
SE415974B (sv) 1980-11-17
ES413175A1 (es) 1976-06-01
EG11137A (en) 1978-06-30
HU169037B (ru) 1976-09-28
SU538662A3 (ru) 1976-12-05
AR207633Q (es) 1976-10-22
US3875176A (en) 1975-04-01
AU469111B2 (en) 1976-02-05
ZA732013B (en) 1974-04-24
RO63441A (fr) 1978-05-15
ES413173A1 (es) 1976-01-16
FR2184077A1 (ru) 1973-12-21
BE799339A (fr) 1973-11-09
CS181238B2 (en) 1978-03-31
IL42007A (en) 1977-06-30
SU561508A3 (ru) 1977-06-05
FR2184077B1 (ru) 1976-07-02
DD106378A5 (ru) 1974-06-12
DE2319872A1 (de) 1973-11-22
ES413174A1 (es) 1976-01-16
GB1416459A (en) 1975-12-03

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