Hydrochloric Acid → N-(5-bromopyridin-2-yl)-4-chloro-3-nitrobenzamide

HRID 605059Notes

Reaction equation

HRID 605059 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.Cl>C1(C)C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 706222-Amino-5-bromopyridineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 5023018N-(5-bromopyridin-2-yl)-4-chloro-3-nitrobenzamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-3-nitrobenzoyl chloride (22.0 g, 0.1 mol) and 2-amino-5-bromopyridine (17.3 g, 0.1 mol) in toluene (250 mL) was refluxed for 4 hours, allowing gaseous HCl to escape the reaction vessel through an open, water cooled condenser. The reaction mixture was cooled to room temperature, diluted with hexanes (200 mL) and filtered to give the title compound (33.9 g, 95%).

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-b64e3dd3f2dd47e7b770e373b736228f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…