Reaction #1256756

Reaction equation

2-amino-5-methylbenzoic acid

propyl chloroformate

→

desired product

Yield 66.3%

2-Propoxy-6-methyl-4H-3,1-benzoxazin-4-one

Yield 66.3%

Solvents

pyridine

Conditions

Workup

1. 1
   Otherafter which time the pyridine was removed in vacuo
2. 2
   WashThe residue was washed with water (25 ml)
3. 3
   Otherdried in vacuo

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 propyl chloroformate (3.0 ml, 26 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 4 h, after which time the pyridine was removed in vacuo. The residue was washed with water (25 ml) and dried in vacuo to afford the desired product as an off-white solid (0.96 g, 66%); 5H (400 MHz, DMSO-d6) 1.03 (3H, t, J 7, CH2CH3), 1.82 (2H, tq, J, J′ 7, CH2CH3), 2.46 (3H, s, CH3), 4.42 (2H, t, J 7, OCH2), 7.40 (1H, d, J 8, Ph), 7.71 (1H, d, J 8, Ph), 7.89 (1H, s, Ph); m/z (ES+) 219 (MH+).

Source