Reaction #1256755

Reaction equation

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

Yield 41.4%

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

Yield 41.4%

Solvents

pyridine

Conditions

Workup

1. 1
   Otherafter which time the pyridine was removed in vacuo
2. 2
   WashThe residue was washed with water (20 ml)
3. 3
   Otherdried in vacuo
4. 4
   OtherRecrystallisation from toluene

Procedure

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