3-Chloro-4-fluorobenzoic acid → 3-chloro-4-fluoro-N-isopropylbenzamide

Reaction equation

Cl.[CH:2]([NH2:5])([CH3:4])[CH3:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[F:16])[C:10](O)=[O:11]>>[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[F:16])[C:10]([NH:5][CH:2]([CH3:4])[CH3:3])=[O:11]

Participants

Reactant 2

HCID 5209893-Chloro-4-fluorobenzoic acid

HCID 64321372-Propanamine, hydrochloride (1:1)

Product 1

HCID 583244933-chloro-4-fluoro-N-isopropylbenzamideYield 81%

Procedure

Using isopropylamine hydrochloride and 3-chloro-4-fluorobenzoic acid in the general procedure for coupling of amines to carboxylic acids, the title compound was obtained (81% yield) as a white solid. ESI-MS: m/z 216 (M+H)+.

Sources & evidence

ORD record: ord-07137750362f4509bb76b0f6bab73557
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822470B2

Reaction notes

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