Réaction #1256755

Équation de réaction

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

Rendement 41.4%

6-Methyl-2-phenoxy-4H-3,1-benzoxazin-4-one

Rendement 41.4%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Autreafter which time the pyridine was removed in vacuo
2. 2
   LavageThe residue was washed with water (20 ml)
3. 3
   Autredried in vacuo
4. 4
   AutreRecrystallisation from toluene

Mode opératoire

A solution of 2-amino-5-methylbenzoic acid (1.0 g, 6.6 mmol) in pyridine (10 ml) was cooled to 0° C. and treated dropwise with phenyl chloroformate (3.3 ml, 26 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 16 h, after which time the pyridine was removed in vacuo. The residue was washed with water (20 ml) and dried in vacuo. Recrystallisation from toluene afforded the desired product as a pale brown solid (692 mg, 41%); δH (400 MHz, DMSO-d6) 2.40 (3H, s, CH3), 7.33-7.45 (3H, m, Ph), 7.48-7.55 (3H, m, Ph), 7.63 (1H, d, J 8, Ph), 7.89 (1H, s, Ph-H5); m/z (ES+) 254 (MH+).

Source