反応 #1256755

反応方程式

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

収率 41.4%

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

収率 41.4%

溶媒

pyridine

反応条件

後処理

1. 1
   その他after which time the pyridine was removed in vacuo
2. 2
   洗浄The residue was washed with water (20 ml)
3. 3
   その他dried in vacuo
4. 4
   その他Recrystallisation from toluene

実験手順

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+).

出典