Water → N-(2-chloro-5-nitrophenyl)-3,4-dimethoxybenzamide

HRID 991418Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[Cl:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH2:17].O>N1C=CC=CC=1>[Cl:14][C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH:17][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3,4-Dimethoxybenzoyl chloride (2 g) was added to a stirred suspension of 2-chloro-5-nitroaniline (1.72 g) in pyridine (10 ml) at 20° C. The reaction mixture was heated to 100° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was poured into water (100 ml). The resulting precipitate was collected, washed with water and dried. The solid was triturated under methylene chloride (20 ml) to give N-(2-chloro-5-nitrophenyl)-3,4-dimethoxybenzamide (1.2 g), m.p. 231-232° C.; NMR Spectrum: (DMSOd6) 3.82 (s, 6H), 7.08 (d, 1H), 7.62 (m, 1H), 7.82 (d, 1H), 8.08 (m, 1H), 8.54 (d, 1H), 10.07 (m, 1H);

Workup

temperatureAfter cooling to ambient temperature
customThe resulting precipitate was collected
washwashed with water
customdried
customThe solid was triturated under methylene chloride (20 ml)

Sources & evidence

ORD record: ord-be5cac2653734e61a10a60d8b32c5330
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465455B1

Reaction notes

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