3,4-Difluorobenzoic acid → 3,4-difluoro-N-methylbenzamide

Reaction equation

Cl.[CH3:2][NH2:3].[F:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8](O)=[O:9]>>[F:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8]([NH:3][CH3:2])=[O:9]

Participants

Reactant 2

HCID 991663,4-Difluorobenzoic acid

HCID 6364545Methylamine hydrochloride

Product 1

HCID 176830103,4-difluoro-N-methylbenzamideYield 75%

Procedure

Using methylamine hydrochloride and 3,4-difluorobenzoic acid in the general procedure for coupling of amines to carboxylic acids (Scheme C), the title compound was obtained (75% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.78 (d, J=4.55 Hz, 3 H) 7.55 (dt, J=10.61, 8.34 Hz, 1 H) 7.72 (dddd, J=8.59, 4.55, 2.15, 1.39 Hz, 1 H) 7.86 (ddd, J=11.68, 7.89, 2.15 Hz, 1 H) 8.48-8.59 (m, 1 H). ESI-MS: m/z 172.1 (M+H)+. mp=142.7-145.0° C.

Sources & evidence

ORD record: ord-6099997a3c3c44d7a9209cbd89cef509
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541417B2

Reaction notes

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