Reaction #68994

Reaction equation

4-Methoxy-benzoyl chloride

2,6-dichloro-pyridin-3-ylamine

water

→

N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamide

Yield 95.0%

Solvents

pyridine

Conditions

Workup

1. 1
   workup.ADDITIONaddition
2. 2
   Temperatureto warm to room temperature
3. 3
   Filtrationwas collected by filtration
4. 4
   WashThe collected solids were washed with additional water
5. 5
   Otherbefore drying overnight in vacuo

Procedure

4-Methoxy-benzoyl chloride (4.15 mL, 30.7 mmol) was added dropwise to a stirred, cooled 0° C. mixture of 2,6-dichloro-pyridin-3-ylamine (5 g, 30.7 mmol) in pyridine (31 mL). Following addition, the reaction mixture was allowed to warm to room temperature and stirring was continued for 30 minutes, at which point the reaction mixture was poured into water causing the formation of a precipitate which was collected by filtration. The collected solids were washed with additional water before drying overnight in vacuo affording N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamide (8.66 g, 29.1 mmol, 95% yield) which was used in subsequent reactions without further purification. ES MS (M+H+)=297.

Source