IL131397A - Method for the production of -5 aminomethyl - 2 chloropyridines - Google Patents

Method for the production of -5 aminomethyl - 2 chloropyridines

Info

Publication number: IL131397A
Authority: IL; Israel
Prior art keywords: chloropyridine; stage; process according; hydrogen; formula
Prior art date: 1997-03-14

Application number

IL13139798A

Other languages

English (en)

Hebrew (he)

Other versions

IL131397A0 (en

Original Assignee

Bayer Ag

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.)

1997-03-14

Filing date

1998-03-02

Publication date

2004-05-12

1998-03-02 Application filed by Bayer Ag filed Critical Bayer Ag

2001-01-28 Publication of IL131397A0 publication Critical patent/IL131397A0/xx

2004-05-12 Publication of IL131397A publication Critical patent/IL131397A/en

Links

XPARFBOWIYMLMY-UHFFFAOYSA-N (6-chloropyridin-3-yl)methanamine Chemical class NCC1=CC=C(Cl)N=C1 XPARFBOWIYMLMY-UHFFFAOYSA-N 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title description 2
238000005660 chlorination reaction Methods 0.000 claims abstract description 16
150000001412 amines Chemical class 0.000 claims abstract description 10
VXLYOURCUVQYLN-UHFFFAOYSA-N 2-chloro-5-methylpyridine Chemical compound CC1=CC=C(Cl)N=C1 VXLYOURCUVQYLN-UHFFFAOYSA-N 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000003085 diluting agent Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 14
SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 abstract description 8
WFTIMXPPHQSLAE-UHFFFAOYSA-N 2-chloro-5-(dichloromethyl)pyridine Chemical compound ClC(Cl)C1=CC=C(Cl)N=C1 WFTIMXPPHQSLAE-UHFFFAOYSA-N 0.000 abstract description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 10
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 5
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
-1 for example Chemical class 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
OZOGUHHRZVXYBW-UHFFFAOYSA-N 2-(chloromethyl)-5-(trichloromethyl)pyridine Chemical compound ClCC1=CC=C(C(Cl)(Cl)Cl)C=N1 OZOGUHHRZVXYBW-UHFFFAOYSA-N 0.000 description 1
FOXDMOFYUBDIFD-UHFFFAOYSA-N 2-(dichloromethyl)pyridine Chemical class ClC(Cl)C1=CC=CC=N1 FOXDMOFYUBDIFD-UHFFFAOYSA-N 0.000 description 1
WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
XPRDCBLXFOSXPD-UHFFFAOYSA-N 2-chloro-3-(dichloromethyl)pyridine Chemical compound ClC(Cl)C1=CC=CN=C1Cl XPRDCBLXFOSXPD-UHFFFAOYSA-N 0.000 description 1
HJQDSJJSRDWZIA-UHFFFAOYSA-N 2-chloro-5-ethylpyridine Chemical compound CCC1=CC=C(Cl)N=C1 HJQDSJJSRDWZIA-UHFFFAOYSA-N 0.000 description 1
UGOBIIKCXGCEKC-UHFFFAOYSA-N 2-chloro-5-methylpyridine;hydrochloride Chemical compound Cl.CC1=CC=C(Cl)N=C1 UGOBIIKCXGCEKC-UHFFFAOYSA-N 0.000 description 1
QMDKBCLEIGIEBO-UHFFFAOYSA-N 3-(trichloromethyl)pyridine Chemical class ClC(Cl)(Cl)C1=CC=CN=C1 QMDKBCLEIGIEBO-UHFFFAOYSA-N 0.000 description 1
QAJYCQZQLVENRZ-UHFFFAOYSA-N 6-chloropyridin-3-amine Chemical compound NC1=CC=C(Cl)N=C1 QAJYCQZQLVENRZ-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
VLDUMLMCDDLHCN-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]ethanamine Chemical compound CCNCC1=CC=C(Cl)N=C1 VLDUMLMCDDLHCN-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)

IL13139798A 1997-03-14 1998-03-02 Method for the production of -5 aminomethyl - 2 chloropyridines IL131397A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19710613A DE19710613A1 (de)	1997-03-14	1997-03-14	Verfahren zur Herstellung von 5-Aminomethyl-2-chlorpyridinen
PCT/EP1998/001163 WO1998041504A1 (fr)	1997-03-14	1998-03-02	Procede de production de 5-aminomethyl-2-chloropyridines

Publications (2)

Publication Number	Publication Date
IL131397A0 IL131397A0 (en)	2001-01-28
IL131397A true IL131397A (en)	2004-05-12

Family

ID=7823387

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13139798A IL131397A (en)	1997-03-14	1998-03-02	Method for the production of -5 aminomethyl - 2 chloropyridines

Country Status (14)

Country	Link
US (1)	US6150528A (fr)
EP (1)	EP0970052B1 (fr)
JP (1)	JP4320059B2 (fr)
KR (1)	KR100486432B1 (fr)
CN (1)	CN1113056C (fr)
AT (1)	ATE273278T1 (fr)
AU (1)	AU6726998A (fr)
BR (1)	BR9808322A (fr)
DE (2)	DE19710613A1 (fr)
DK (1)	DK0970052T3 (fr)
ES (1)	ES2227819T3 (fr)
HU (1)	HUP0001596A3 (fr)
IL (1)	IL131397A (fr)
WO (1)	WO1998041504A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL150622A0 (en) *	2000-01-19	2003-02-12	Bayer Ag	Method for producing heterocyclic compounds
TW200900399A (en) *	2003-10-01	2009-01-01	Speedel Experimenta Ag	Organic compounds
KR100952201B1 (ko)	2009-07-10	2010-04-09	주식회사 엘에스텍	레이저를 이용한 패턴형성장치
KR100935387B1 (ko)	2009-07-10	2010-01-06	주식회사 엘에스텍	레이저를 이용한 패턴형성장치
KR100952202B1 (ko)	2009-09-11	2010-04-09	주식회사 엘에스텍	도광판용 패턴형성장치
EP3696168B1 (fr) *	2018-01-05	2022-09-21	Zhejiang Lantian Environmental Protection Hi-Tech Co., Ltd.	Procédé de préparation de 2-chloro-5-trifluorométhylpyridine

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZW5085A1 (en) *	1984-04-13	1985-09-18	Nihon Tokushu Noyaku Seizo Kk	Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides
DE3630046A1 (de) *	1986-09-04	1988-03-17	Bayer Ag	Verfahren zur herstellung von 5-chlormethylpyridinen
DE4016175A1 (de) *	1990-05-19	1991-11-21	Bayer Ag	Seitenkettenchlorierung von alkylierten stickstoff-heteroaromaten
JP2823414B2 (ja) *	1992-02-26	1998-11-11	セントラル硝子株式会社	２−クロロ−メチルピリジン類の側鎖塩素化法
JP3098100B2 (ja) *	1992-04-17	2000-10-10	広栄化学工業株式会社	２−クロロ−５−アミノメチルピリジン類の製造方法
ES2114623T3 (es) *	1993-02-01	1998-06-01	Koei Chemical Co	Procedimiento para preparar 2-cloro-5-aminometil-piridinas.

1997
- 1997-03-14 DE DE19710613A patent/DE19710613A1/de not_active Withdrawn
1998
- 1998-03-02 BR BR9808322-8A patent/BR9808322A/pt not_active IP Right Cessation
- 1998-03-02 CN CN98803333A patent/CN1113056C/zh not_active Expired - Lifetime
- 1998-03-02 HU HU0001596A patent/HUP0001596A3/hu unknown
- 1998-03-02 US US09/380,955 patent/US6150528A/en not_active Expired - Lifetime
- 1998-03-02 WO PCT/EP1998/001163 patent/WO1998041504A1/fr not_active Ceased
- 1998-03-02 EP EP98912427A patent/EP0970052B1/fr not_active Expired - Lifetime
- 1998-03-02 IL IL13139798A patent/IL131397A/en not_active IP Right Cessation
- 1998-03-02 AU AU67269/98A patent/AU6726998A/en not_active Abandoned
- 1998-03-02 JP JP54006798A patent/JP4320059B2/ja not_active Expired - Lifetime
- 1998-03-02 ES ES98912427T patent/ES2227819T3/es not_active Expired - Lifetime
- 1998-03-02 DE DE59811798T patent/DE59811798D1/de not_active Expired - Lifetime
- 1998-03-02 KR KR10-1999-7007584A patent/KR100486432B1/ko not_active Expired - Lifetime
- 1998-03-02 DK DK98912427T patent/DK0970052T3/da active
- 1998-03-02 AT AT98912427T patent/ATE273278T1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP0001596A3 (en)	2002-01-28
EP0970052A1 (fr)	2000-01-12
JP4320059B2 (ja)	2009-08-26
KR20000075525A (ko)	2000-12-15
EP0970052B1 (fr)	2004-08-11
BR9808322A (pt)	2000-05-16
DK0970052T3 (da)	2004-12-20
IL131397A0 (en)	2001-01-28
ATE273278T1 (de)	2004-08-15
JP2001515496A (ja)	2001-09-18
DE19710613A1 (de)	1998-09-17
DE59811798D1 (de)	2004-09-16
KR100486432B1 (ko)	2005-04-29
CN1250439A (zh)	2000-04-12
ES2227819T3 (es)	2005-04-01
HUP0001596A2 (hu)	2000-09-28
WO1998041504A1 (fr)	1998-09-24
AU6726998A (en)	1998-10-12
CN1113056C (zh)	2003-07-02
US6150528A (en)	2000-11-21

Legal Events

Date	Code	Title
2004-09-27	FF	Patent granted
2004-11-10	KB	Patent renewed
2008-04-13	KB	Patent renewed
2012-03-29	KB	Patent renewed
2016-02-29	KB	Patent renewed
2018-10-31	EXP	Patent expired

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