JPS632262B2 - - Google Patents

Info

Publication number: JPS632262B2
Authority: JP; Japan
Prior art keywords: cyanopyridine; phosphorus oxychloride; oxide; chloro; reaction
Prior art date: 1980-06-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP7471880A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56169672A (en

Inventor

Fumya Harada

Nanao Watanabe

Toshiaki Kataoka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Koei Chemical Co Ltd

Original Assignee

Koei Chemical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-06-02

Filing date

1980-06-02

Publication date

1988-01-18

1980-06-02 Application filed by Koei Chemical Co Ltd filed Critical Koei Chemical Co Ltd

1980-06-02 Priority to JP7471880A priority Critical patent/JPS56169672A/ja

1981-12-26 Publication of JPS56169672A publication Critical patent/JPS56169672A/ja

1988-01-18 Publication of JPS632262B2 publication Critical patent/JPS632262B2/ja

Status Granted legal-status Critical Current

Links

XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 52
JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 claims description 21
WOOVSQCALYYUDO-UHFFFAOYSA-N 1-oxidopyridin-1-ium-3-carbonitrile Chemical compound [O-][N+]1=CC=CC(C#N)=C1 WOOVSQCALYYUDO-UHFFFAOYSA-N 0.000 claims description 17
IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 8
230000003301 hydrolyzing effect Effects 0.000 claims 2
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 26
238000000034 method Methods 0.000 description 22
239000000243 solution Substances 0.000 description 13
239000013078 crystal Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
RXTRRIFWCJEMEL-UHFFFAOYSA-N 2-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1Cl RXTRRIFWCJEMEL-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000002994 raw material Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000000297 Sandmeyer reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
-1 nicotinic acid amide N-oxide Chemical compound 0.000 description 2
FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XXDJXMMIVUCDGP-UHFFFAOYSA-N 1-oxidopyridin-1-ium-2-carbonitrile Chemical compound [O-][N+]1=CC=CC=C1C#N XXDJXMMIVUCDGP-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
244000309464 bull Species 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

JP7471880A 1980-06-02 1980-06-02 Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid Granted JPS56169672A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP7471880A JPS56169672A (en)	1980-06-02	1980-06-02	Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7471880A JPS56169672A (en)	1980-06-02	1980-06-02	Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid

Publications (2)

Publication Number	Publication Date
JPS56169672A JPS56169672A (en)	1981-12-26
JPS632262B2 true JPS632262B2 (no)	1988-01-18

Family

ID=13555273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7471880A Granted JPS56169672A (en)	1980-06-02	1980-06-02	Preparation of 2-chloro-3-cyanopyridine and 2- chloronicotinic acid

Country Status (1)

Country	Link
JP (1)	JPS56169672A (no)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4504665A (en) *	1982-04-12	1985-03-12	Ishihara Sangyo Kaisha Ltd.	Process for producing chloronicotinic acid compounds
JPS59144759A (ja) *	1983-02-07	1984-08-18	Yuki Gosei Yakuhin Kogyo Kk	２−クロロニコチン酸の製造方法
CN104072409B (zh) *	2014-06-27	2016-08-24	温州大学	一种吡啶酰胺类化合物的合成方法
CN109836376B (zh) *	2019-04-10	2022-03-22	江苏汉阔生物有限公司	一种以2，3-吡啶二羧酸为原料制备2-氯代烟酸的方法

1980
- 1980-06-02 JP JP7471880A patent/JPS56169672A/ja active Granted

Also Published As

Publication number	Publication date
JPS56169672A (en)	1981-12-26

Publication	Publication Date	Title
US3644380A (en)	1972-02-22	Preparation of 3-cyanopyridine
JPS632262B2 (no)	1988-01-18
TW585855B (en)	2004-05-01	A novel production method for maleimides
EP1424328B1 (en)	2005-11-09	Process for producing 4-dimethyl amino pyridine (4-DMAP)
JPH0449544B2 (no)	1992-08-11
JP3029894B2 (ja)	2000-04-10	新規な２−ヒドロキシメチル−４−メトキシ−３，５−ジメチルピリジンの製造方法及びその製造中間体ならびにそれらの製造法
JPH0822851B2 (ja)	1996-03-06	２，３，５−トリクロロピリジンの製造方法
JPS63297367A (ja)	1988-12-05	９−アミノ−２，３，５，６，７，８−ヘキサヒドロ−１Ｈ−シクロペンタ（ｂ）キノリンの製造方法
JP3592747B2 (ja)	2004-11-24	Ｎ−ｔｅｒｔ−ブチル−２，３−ピラジンジカルボキサミド及びその製造法
WO1995023787A1 (fr)	1995-09-08	Procede de production de 5,7-dichloro-4-hydroxyquinoleine
JPH07304726A (ja)	1995-11-21	２−アリール−エタン−スルホン酸類の製造方法
JPH03223252A (ja)	1991-10-02	置換メチルアミン類の製造方法
JPS6316374B2 (no)	1988-04-08
JP2767295B2 (ja)	1998-06-18	インドール―３―カルボニトリル化合物の製造方法
JP2560431B2 (ja)	1996-12-04	２，４−ジヒドロキシアセトフェノンの製造法
JPS62187467A (ja)	1987-08-15	４−アセチルイソキノリノン化合物の新規製造法
US4216325A (en)	1980-08-05	4-(p-Fluorobenzoyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine
JPS58172389A (ja)	1983-10-11	１，２，５，６−テトラヒドロ−４−Ｈ−ピロロ〔３，２，１−ｉｊ〕−キノリン−４−オンの製造方法
JPH06199809A (ja)	1994-07-19	２，５−ジブロモピリミジンの製造法
KR900007370B1 (ko)	1990-10-08	2,4-디브로모-5-플루오르벤조산 및 그 제조방법
JPH07145162A (ja)	1995-06-06	４ｈ−ピラン−４−オンの製造方法
JPS6155503B2 (no)	1986-11-28
JPS59163370A (ja)	1984-09-14	Ｏ−（アミノメチル）フエニル酢酸ラクタムの製造方法
JPS6028976A (ja)	1985-02-14	ピペリジリデンメタン第４級塩の製法
JPS62181268A (ja)	1987-08-08	ピラジン−ｎ−オキサイド類の製造法