Reacción #1256755

Ecuación de reacción

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

Rendimiento 41.4%

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

Rendimiento 41.4%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroafter which time the pyridine was removed in vacuo
2. 2
   LavadoThe residue was washed with water (20 ml)
3. 3
   Otrodried in vacuo
4. 4
   OtroRecrystallisation from toluene

Procedimiento

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+).

Fuente