تفاعل #417956

معادلة التفاعل

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

المردود 41.4%

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

المردود 41.4%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىafter which time the pyridine was removed in vacuo
2. 2
   غسيلThe residue was washed with water (20 ml)
3. 3
   أخرىdried in vacuo
4. 4
   أخرىRecrystallisation from toluene

الإجراء التجريبي

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+).

المصدر