Ethylamine hydrochloride → 3-chloro-4-fluoro-N-ethylbenzamide

HRID 69692

Reaction equation

Cl.[CH2:2]([NH2:4])[CH3:3].[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([OH:11])=O>>[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([NH:4][CH2:2][CH3:3])=[O:11]

Participants

Reactant 2

HCID 11198Ethylamine hydrochloride

HCID 5209893-Chloro-4-fluorobenzoic acid

Product 1

HCID 187119593-chloro-4-fluoro-N-ethylbenzamideYield 77%

Procedure

Using ethanamine hydrochloride and 3-chloro-4-fluorobenzoic acid in the general procedure for coupling of amines to carboxylic acids, the title compound was obtained (77% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (t, J=7.20 Hz, 3 H) 3.28 (qd, J=7.16, 5.56 Hz, 2 H) 7.53 (t, J=8.84 Hz, 1 H) 7.87 (ddd, J=8.72, 4.80, 2.15 Hz, 1 H) 8.06 (dd, J=7.33, 2.27 Hz, 1 H) 8.61 (t, J=4.67 Hz, 1 H). ESI-MS: m/z 202.0 (M+H)+. mp=101.7-101.8° C.

Sources & evidence

ORD record: ord-0871c5c452864493a48a82196c401cb9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822470B2

Linked notes

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