Reaktion #417956

Reaktionsgleichung

2-amino-5-methylbenzoic acid

phenyl chloroformate

→

desired product

Ausbeute 41.4%

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

Ausbeute 41.4%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeafter which time the pyridine was removed in vacuo
2. 2
   WaschenThe residue was washed with water (20 ml)
3. 3
   Sonstigedried in vacuo
4. 4
   SonstigeRecrystallisation from toluene

Vorschrift

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+).

Quelle