2-Nitrobenzoyl chloride → n-(2-Chloropyridin-3-yl)-2-nitrobenzamide

HRID 1258038Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[Cl:13][C:14]1[C:19]([NH2:20])=[CH:18][CH:17]=[CH:16][N:15]=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:20][C:19]1[C:14]([Cl:13])=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:7])([O-:3])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-nitrobenzoylchloride (7.2 g) in 100 ml toluene was added dropwise to a stirring solution of 2-chloro-3-amino-pyridine (10.0 g) in 100 ml toluene. After the entire amount was added, the mixture was heated to 80° C. for 120 min. After the reaction mixture was cooled down and the resulting 2-nitro-N-(2-chloro-pyridin-3-yl)-benzamide was isolated by filtration. Yield 10.0 g, mp 158-161° C.

Workup

additionAfter the entire amount was added
temperatureAfter the reaction mixture was cooled down

Sources & evidence

ORD record: ord-088eb384941c46d2a73f48c95dcfb3cb
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466144B2

Reaction notes

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