Pyridine → N-(5-chloropyridin-2-yl)-5-methyl-2-nitrobenzamide

HRID 12153

Reaction equation

HRID 12153 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:7]([C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[O:9])=[N:22][CH:23]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 183715-Methyl-2-nitrobenzoic acidHCID 65578Oxalyl chlorideHCID 661742-Amino-5-chloropyridine

Product 1

HCID 3562519N-(5-chloropyridin-2-yl)-5-methyl-2-nitrobenzamideYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methyl-2-nitrobenzoic acid (1 g, 5.52 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.964 ml, 11.04 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-chloropyridine (852 mg, 6.62 mmol) and pyridine (1.34 ml, 16.56 mmol) were added to the solution. The mixture was stirred at r.t. overnight. After the evaporation of the solvent, the crude residue was purified by silica gel column chromatography using solvent system 25% ethyl acetate in hexane as eluent to give N-(5-chloro(2-pyridyl))(5-methyl-2-nitrophenyl)carboxamide as a solid (1.48 g, 92%). MS found for C13H10ClN3O3 M+=291, (M+2)+=293.

Workup

  1. customAfter the evaporation of the solvent
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred at r.t. overnight
  4. customAfter the evaporation of the solvent
  5. customthe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd09f05c6fa3401a81f8a51176430386
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Linked notes

Loading…