KR880006168A - 5,6-디히드록시인돌과 이의 3-알킬유도체 그리고 이의 중간 물질의 제조 방법 - Google Patents

5,6-디히드록시인돌과 이의 3-알킬유도체 그리고 이의 중간 물질의 제조 방법 Download PDF

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KR880006168A
KR880006168A KR1019870012500A KR870012500A KR880006168A KR 880006168 A KR880006168 A KR 880006168A KR 1019870012500 A KR1019870012500 A KR 1019870012500A KR 870012500 A KR870012500 A KR 870012500A KR 880006168 A KR880006168 A KR 880006168A
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죄니뇨 알렉스
반덴보쉬 쟝-작끄
랑 게라드
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안드레 뷰오트
로레알
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C07C255/43—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/08—Material containing basic nitrogen containing amide groups using oxidation dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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  • Indole Compounds (AREA)
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract

내용 없음

Description

5,6-디히드록시인돌과 이의 3-알킬유도체 그리고 이의 중간 물질의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. 용매매체에서 그리고 수소화촉매의 존재하에, 일반식(2)의 화합물을 압력하에서 수소의 작용에 처리하거나 또는 수소이전이 조작 처리하여, 5,6-디히드록시인돌이나 또는 이의 3-알킬 유도체를 제조하는 방법:
    이식에서 R'는 수소원자 또는 임의로 치환한 벤질라디칼을 나타내고, 그리고 R"는 수소나 또는 알킬을 나타낸다.
  2. 제 1항에 있어서, 수소반응이 105내지 106파스칼, 바람직하게는 4×105내지 6×106파스칼의 압력하에서 실시되는 방법.
  3. 제 1항에 있어서, 수소반응이 50 내지 150˚C, 바람직하게는 80 내지 100˚C의 온도에서 실시되는 방법.
  4. 제 1항에 있어서, 수소전이를 시클로헥센을 사용하여 실시하는 방법.
  5. 제 1항에 있어서, 용매매체가 반응에 관여하지 않은 용매나 또는 용매혼합물로되고, 그리고 알코올, 에스테르, 디메틸포름 알데히드, 테트라히드로푸란, 디옥산, 디글림(diglym)및 물과 이들과의 혼합물에서 선택하는 방법.
  6. 제 1항에 있어서, 촉매를 비활성 담체에 있는 팔라듐이나 또는 로듐에서 선택하는 방법.
  7. 제 6항에 있어서, 담체가 목탄으로 구성되는 방법.
  8. 제 1항에 있어서, 일반식(2)의 화합물이 단일의 탈벤질화 및 환형성단계에서 5,6-디히드록시인돌로 전환된 4,5-디벤질옥시-2-니트로페닐아세트로니트릴인 방법.
  9. 일반식(3)에 사용하는 신규의 화합물:
    이식에서 R'는 수소원자 또는 임의로 치환된 벤질라디칼을 나타내고 그리고, R"는 수소나 또는 알킬라디칼을 나타낸다.
  10. 일반식(3)에 상응하는 신규의 화합물:
    이식에서 R"는 수소 또는 알킬라디칼을 나타낸다.
  11. 일반식(6)의 4,5-디벤질옥시페닐아세로니트릴을 얻기 위하여 용매 그리고 알칼리매체의 존재하에 일반식(5)의 4,5-디히드록시페닐아세토니트릴을 할로겐화벤질과 반응시키고:
    일반식(2)의 화합물을 제조하기 위하여 이 화합물을 니트로화 반응 처리하여, 일반식(2)에 상응하는 화합물을 제조하는 방법: 일반식(2)에서 R'는 임의로 치환된 벤질라디칼을 나타내고 그리고 R"는 수소를 나타낸다.
  12. 제 11항에 있어서, 수득된 화합물을 수소전이를 이용하여 탈벤질화 반응시켜 일반식(2)의 화합물을 만드는 방법: 일반식(2)에서, R'는 H를 나타내고 그리고 R"는 수소를 나타낸다.
  13. 제 11항에 있어서, 일반식(5)의 화합물을 피린딘 염화수소의 방법에 의하여 다음 일반식의 호모베라트로니트릴을 탈메틸화하여 제조 하는 방법:
  14. 제 13항에 있어서, 피리딘 염화수소를 원위치에서 제조하고 염화수소의 첨가에 의한 반응중에 재생시키는 방법.
  15. 제 1항에 있어서, 일반식(2)의 화합물을 제 11항 내지 제 14항중 어느 한항에서 정의한 것과 같은 방법으로 제조하는 방법.
  16. 알칼리제의 존재하에 한용매 매체에서 R'이 벤질이고 R"가 수소로된 일반식(2)의 화합물에 할로겐화알킬을 반응시키는 것을 포함하는, R"가 알킬을 가르키게된 일반식(2)의 화합물을 제조하는 방법.
  17. 케라틴 섬유 그리고 특별히 인체모발을 염색하기 위한 제 1항에 따라 제조한 화합물의 사용.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR87012500A 1986-11-07 1987-11-06 Process for the preparation of 5,6-dihydroxy indole and its 3-alkyl derivative and intermediate compounds KR970002746B1 (en)

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US92772386A 1986-11-07 1986-11-07
FR927723 1986-11-07

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JP (1) JP2553108B2 (ko)
KR (1) KR970002746B1 (ko)
CN (1) CN1019972C (ko)
AR (1) AR245695A1 (ko)
AT (1) AT390950B (ko)
AU (1) AU604780B2 (ko)
BE (1) BE1000762A5 (ko)
BR (1) BR8705980A (ko)
CA (2) CA1300633C (ko)
CH (2) CH679150A5 (ko)
DE (1) DE3737825A1 (ko)
ES (1) ES2007747A6 (ko)
FR (1) FR2606405B1 (ko)
GB (1) GB2198128B (ko)
GR (1) GR871701B (ko)
IT (1) IT1211506B (ko)
NL (1) NL8702660A (ko)
PT (1) PT86088B (ko)
ZA (1) ZA878313B (ko)

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YU213587A (en) * 1986-11-28 1989-06-30 Orion Yhtymae Oy Process for obtaining new pharmacologic active cateholic derivatives
US5283352A (en) * 1986-11-28 1994-02-01 Orion-Yhtyma Oy Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same
US5489614A (en) * 1987-11-27 1996-02-06 Orion-Yhtyma Oy Catechol derivatives, their physiologically acceptable salts, esters and use
DE4204089A1 (de) * 1992-02-12 1993-08-19 Henkel Kgaa Synthese von indolen durch dehydrierung von indolinen
US5262546A (en) * 1992-11-17 1993-11-16 Clairol, Inc. Process for the preparation of 5,6-diacetoxyindole
FR2742162B1 (fr) 1995-12-06 1998-01-16 Oreal Procede de preparation de composes indoliques
US6160127A (en) * 1998-07-15 2000-12-12 Bristol-Myers Squibb Company Process for the preparation of substituted indoles
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US6384263B1 (en) * 2000-08-04 2002-05-07 E. I. Du Pont De Nemours And Company Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane
CN102976957A (zh) * 2012-11-30 2013-03-20 四川大学 一种制备4-氨基邻苯二酚的方法
CN103073495B (zh) * 2013-02-06 2015-08-05 苏州立新制药有限公司 一种ent-3-甲氧基吗喃的制备方法
WO2019088151A1 (ja) * 2017-11-01 2019-05-09 花王株式会社 ジヒドロキシインドール類の製造方法
CN114805126B (zh) * 2022-05-03 2024-06-18 浙江荣耀生物科技股份有限公司 2-硝基-4,5-二苄氧基苯乙腈的制备方法

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US5498746A (en) 1996-03-12
ES2007747A6 (es) 1989-07-01
AR245695A1 (es) 1994-02-28
AT390950B (de) 1990-07-25
CN87107372A (zh) 1988-08-03
PT86088A (fr) 1987-12-01
GB8726173D0 (en) 1987-12-16
JPS63135365A (ja) 1988-06-07
GR871701B (en) 1988-03-04
AU8087087A (en) 1988-06-02
NL8702660A (nl) 1988-06-01
CA1300643C (fr) 1992-05-12
US5508464A (en) 1996-04-16
GB2198128B (en) 1990-11-07
DE3737825C2 (ko) 1990-05-31
BE1000762A5 (fr) 1989-03-28
CH676845A5 (ko) 1991-03-15
KR970002746B1 (en) 1997-03-10
FR2606405A1 (fr) 1988-05-13
GB2198128A (en) 1988-06-08
ZA878313B (en) 1989-07-26
IT1211506B (it) 1989-11-03
BR8705980A (pt) 1988-06-14
US5536865A (en) 1996-07-16
AU604780B2 (en) 1991-01-03
FR2606405B1 (fr) 1995-06-23
CH679150A5 (ko) 1991-12-31
JP2553108B2 (ja) 1996-11-13
US5410067A (en) 1995-04-25
CN1019972C (zh) 1993-03-03
ATA294087A (de) 1990-01-15
CA1300633C (fr) 1992-05-12
DE3737825A1 (de) 1988-05-19
PT86088B (pt) 1990-11-20
IT8767951A0 (it) 1987-11-06

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