تفاعل #40404

معادلة التفاعل

5-methyl-2-nitrobenzoic acid

oxalyl chloride

2-amino-5-chloropyridine

pyridine

→

N-(5-chloro(2-pyridyl))(5-methyl-2-nitrophenyl)carboxamide

المردود 92.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter the evaporation of the solvent
2. 2
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (5 ml)
3. 3
   workup.STIRRINGThe mixture was stirred at r.t. overnight
4. 4
   أخرىAfter the evaporation of the solvent
5. 5
   أخرىthe crude residue was purified by silica gel column chromatography

الإجراء التجريبي

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.

المصدر