Реакция #417956

Уравнение реакции

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

Выход 41.4%

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

Выход 41.4%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   Другоеafter which time the pyridine was removed in vacuo
2. 2
   ПромывкаThe residue was washed with water (20 ml)
3. 3
   Другоеdried in vacuo
4. 4
   ДругоеRecrystallisation from toluene

Методика

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+).

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