WO2009090669A3 - A process for the preparation of 5-chloro-2(2,4-dichlorophenoxy) aniline - Google Patents

A process for the preparation of 5-chloro-2(2,4-dichlorophenoxy) aniline Download PDF

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Publication number
WO2009090669A3
WO2009090669A3 PCT/IN2008/000659 IN2008000659W WO2009090669A3 WO 2009090669 A3 WO2009090669 A3 WO 2009090669A3 IN 2008000659 W IN2008000659 W IN 2008000659W WO 2009090669 A3 WO2009090669 A3 WO 2009090669A3
Authority
WO
WIPO (PCT)
Prior art keywords
ammonium formate
hydrogenation
reduction
high pressure
hydrogenolysis
Prior art date
Application number
PCT/IN2008/000659
Other languages
French (fr)
Other versions
WO2009090669A2 (en
Inventor
Mahesh Subramaniyam
Abhay Bhalchandra Deshpande
Original Assignee
Dorf Ketal Chemicals (I) Private Limited
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.)
Filing date
Publication date
Application filed by Dorf Ketal Chemicals (I) Private Limited filed Critical Dorf Ketal Chemicals (I) Private Limited
Priority to EP08870546A priority Critical patent/EP2209763A2/en
Publication of WO2009090669A2 publication Critical patent/WO2009090669A2/en
Publication of WO2009090669A3 publication Critical patent/WO2009090669A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A novel process for the selective reduction of halonitroarenes in general and halonitroaromatic arenes in particular, without the hydrogenolysis of the C-Cl (where, X represents F-, Cl-, Br- and I) and the C-O-C bonds, in the presence of platinum based catalysts and ammonium formate. The invention makes the use of duel function of ammonium formate, as a hydrogen source for partial reduction (catalytic transfer hydrogenation) and as an additive controlling the hydrogenolysis side reactions during the completion of the reduction by high pressure catalytic hydrogenation using external hydrogen gas source. Uniqueness of the invention lies in the fact that either the catalytic transfer hydrogenation with ammonium formal e or high pressure catalytic hydrogenation in the absence of ammonium formate, when used alone result in lower purity of the said amine. This invention -product is used to synthesize intermediates for making antibacterial compounds.
PCT/IN2008/000659 2007-10-12 2008-10-10 A process for the preparation of 5-chloro-2(2,4-dichlorophenoxy) aniline WO2009090669A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08870546A EP2209763A2 (en) 2007-10-12 2008-10-10 A process for the preparation of 5-chloro-2(2,4-dichlorophenoxy) aniline

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2029MU2007 2007-10-12
IN2029/MUM/2007 2007-10-12

Publications (2)

Publication Number Publication Date
WO2009090669A2 WO2009090669A2 (en) 2009-07-23
WO2009090669A3 true WO2009090669A3 (en) 2009-09-11

Family

ID=40790453

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000659 WO2009090669A2 (en) 2007-10-12 2008-10-10 A process for the preparation of 5-chloro-2(2,4-dichlorophenoxy) aniline

Country Status (2)

Country Link
EP (1) EP2209763A2 (en)
WO (1) WO2009090669A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108218729A (en) * 2018-02-28 2018-06-29 江苏优普生物化学科技股份有限公司 The method that hydrogenating reduction synthesizes 2,4,4 '-three chloro- 2 '-amino-diphenylethers
CN115043734A (en) * 2022-07-26 2022-09-13 山东奥友生物科技股份有限公司 Continuous production process of 2,4,4 '-trichloro-2' -nitrodiphenyl ether

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3546297A (en) * 1969-07-01 1970-12-08 Du Pont Process for preparation of aromatic chloroamines
US4070401A (en) * 1972-02-19 1978-01-24 Mitsui Toatsu Chemicals Inc. Method for the preparation of a halogenated aromatic amine
WO1996036597A1 (en) * 1995-05-19 1996-11-21 Novartis Ag Process for the catalytic hydrogenation of aromatic nitro compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3546297A (en) * 1969-07-01 1970-12-08 Du Pont Process for preparation of aromatic chloroamines
US4070401A (en) * 1972-02-19 1978-01-24 Mitsui Toatsu Chemicals Inc. Method for the preparation of a halogenated aromatic amine
WO1996036597A1 (en) * 1995-05-19 1996-11-21 Novartis Ag Process for the catalytic hydrogenation of aromatic nitro compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GOWDA D C MAHESH B: "Catalytic transfer hydrogenation of aromatic nitro compounds by employing ammonium formate and 5% platinum on carbon", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS GROUP, PHILADELPHIA, PA, vol. 30, no. 20, 1 January 2000 (2000-01-01), pages 3639 - 3644, XP002955633, ISSN: 0039-7911 *

Also Published As

Publication number Publication date
EP2209763A2 (en) 2010-07-28
WO2009090669A2 (en) 2009-07-23

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