Reaction #3353

Reaction equation

dimethylformamide

2-chloro-5-nitrobenzoic acid

dichloromethane

oxalyl chloride

→

2-Chloro-5-nitrobenzamide

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was redissolved in 200 mL of dichloromethane
3. 3
   TemperatureThe solution was cooled to 0° C.
4. 4
   Otherammonia was bubbled through the cold solution for 5 minutes, whereupon the product
5. 5
   Otherprecipitated
6. 6
   Otherto form solution
7. 7
   FiltrationThe product was collected by filtration
8. 8
   Otherto yield 6.8 g, mp 174°-175° C.

Procedure

A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) and 200 mL of dichloromethane was reacted with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. The mixture was stirred at 25° C. for 3 hours. The solvent was removed in vacuo, and the residue was redissolved in 200 mL of dichloromethane. The solution was cooled to 0° C., and ammonia was bubbled through the cold solution for 5 minutes, whereupon the product precipitated to form solution. The product was collected by filtration to yield 6.8 g, mp 174°-175° C.

Source