# US 10,766,859 B2 · Catalytic hydrogenation of nitriles

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- Number: US 10,766,859 B2
- Document ID: US10766859B2
- Status: Granted
- Kind: B2
- Application number: 16/471,144
- Filed: 2017-12-18
- Published: 2020-02-06
- Granted: 2020-09-08
- Earliest claimed: 2016-12-21
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience Aktiengesellschaft
- Inventors: Wahed Ahmed Moradi; Thomas Himmler; Thomas Norbert Mueller
- Web page: https://patentgrep.com/patent/US10766859B2

## CPC

- C07D 213/26: Radicals substituted by halogen atoms or nitro radicals
- C07D 213/40: Acylated substituent nitrogen atom
- C07D 213/60: 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
- C07D 213/61: Halogen atoms or nitro radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to a novel catalytic hydrogenation of substituted 2-methyl cyanopyridyl derivatives, in particular 3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetonitrile [=Py-CN] to substituted 2-ethylaminopyridine derivatives, in particular 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine [=Py-ethanamine] or salts thereof in the presence of Raney catalysts, in particular Raney nickel or cobalt.

## Claims

### Claim 1

A process for preparing 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine or corresponding salts thereof,
comprising
(A1) hydrogenating [3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetonitrile in the presence of Raney cobalt catalyst.

### Claim 2 (depends on 1)

The process according to claim 1 further comprising (A2) reacting the 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine obtained in step (A1) with a benzoyl halide according to formula (IV)
wherein
Hal is fluorine, chlorine or bromine;
q is an integer equal to 1, 2, 3 or 4; and each substituent Y is chosen, independently of the others, as being halogen,
C1-C4 alkyl or C1-C4 haloalkyl; to produce a compound having the formula
wherein
q is an integer equal to 1, 2, 3 or 4; and
each substituent Y is independently halogen,
C1-C4 alkyl or C1-C4 haloalkyl.