Reacción #446714

Ecuación de reacción

ammonia

2-amino-5-methylbenzoic acid

tetrahydrofuran

→

2-amino-5-methylbenzamide

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 24 hours
2. 2
   Concentraciónthe mixture was concentrated under reduced pressure to a solid residue
3. 3
   workup.DISSOLUTIONThis solid Was partially dissolved in 500 ml of dichloromethane
4. 4
   Lavadowashed with 200 ml of 0.1 N sodium hydroxide and 200 ml of water
5. 5
   SecadoThe dichloromethane solution was dried
6. 6
   Concentraciónconcentrated to a solid Which
7. 7
   OtroWas crystallized from ethyl acetate/hexane

Procedimiento

A mixture of 15 g of 2-amino-5-methylbenzoic acid, 16 g of 1,1-carbonyldiimidazole and 500 ml of tetrahydrofuran was stirred for 2 hours at room temperature and then saturated with anhydrous ammonia with ice bath cooling. After 24 hours, 50 ml of water was added and the mixture was concentrated under reduced pressure to a solid residue. This solid Was partially dissolved in 500 ml of dichloromethane and then washed with 200 ml of 0.1 N sodium hydroxide and 200 ml of water. The dichloromethane solution was dried and concentrated to a solid Which Was crystallized from ethyl acetate/hexane, giving 3.0 g of 2-amino-5-methylbenzamide as straw-colored crystals, mp 171°-174° C.

Fuente