Pyridine → N-(5-bromopyridin-2-yl)-2-nitrobenzamide

HRID 12149

Reaction equation

HRID 12149 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].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])=[O:7])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 679218N-(5-bromopyridin-2-yl)-2-nitrobenzamideYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-nitrobenzoyl chloride (3.70 g, 20 mmol, 1.0 equiv), 2-amino-5-bromopyridine (3.50 g, 1.0 equiv), pyridine (10 mL) in 25 mL of methylene chloride was stirred overnight. The volatile was evaporated, flash chromatography on silica gel gave N-(5-bromo-2-pyridinyl)-(2-nitro)phenylcarboxamide (5.02 g, 77%). MS found for C12H9BrN3O3 (M+H)+: 322.

Workup

  1. customThe volatile was evaporated

Sources & evidence

ORD record
ord-aff4bb6560f44a6c9e3a0009d8d22301
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Linked notes

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