Réaction #1269880

Équation de réaction

4-chloronicotinic acid

aniline

→

4-(phenylamino)nicotinic acid

Rendement 99.0%

Solvants

MeCN

Conditions de réaction

Traitement

1. 1
   FiltrationThe solid material was filtered off
2. 2
   Autrethe solvent was removed in vacuo

Mode opératoire

A mixture of 4-chloronicotinic acid (150 mg, 0.952 mmol) and aniline (177 mg, 1.90 mmol) in MeCN (2 mL) was stirred and heated in the microwave (80° C., 300 W) for 1 h. The solid material was filtered off and the solvent was removed in vacuo. The crude 4-(phenylamino)nicotinic acid (202 mg) obtained was dissolved in THF (25 mL). After dropwise addition of LiAlH4 (1 M solution in THF, 3.77 mL, 3.77 mmol) at 0° C., the reaction mixture was stirred for 30 min, allowed to warm to room temperature and stirred overnight. The reaction was quenched with water (0.4 mL) at 0° C. and excess EtOAc was added. All solid material was filtered off and the solvent was removed in vacuo. Trituration with Et2O provided (4-(phenylamino)pyridin-3-yl)methanol (115 mg, 60% over 2 steps). ESI-MS [M+H]+=201.1.

Source