تفاعل #417955

معادلة التفاعل

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

المردود 25.0%

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

المردود 25.0%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   غسيلThis solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىthe solvent removed in vacuo
6. 6
   أخرىto afford a pale orange oily solid
7. 7
   أخرىRecrystallisation from hexane

الإجراء التجريبي

A solution of 2-amino-5-methylbenzoic acid (302 mg, 2 mmol) in pyridine (10 ml) was cooled to 0° C. and treated dropwise with octyl chloroformate (1.15 ml, 6 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 4 h. The pyridine was removed under vacuum and the residue dissolved in ethyl acetate (50 ml). This solution was washed with 1M HCl (10 ml) and brine (5 ml), dried (MgSO4) and the solvent removed in vacuo to afford a pale orange oily solid. Recrystallisation from hexane afforded the desired product as an off-white solid (144 mg, 25%); δH (400 MHz, DMSO-d6) 0.68 (3H, t, J 7, CH2CH3), 1.26-1.40 (10H, m, 5×CH2), 1.73 (2H, tt, J, J′7, OCH2CH2), 2.35 (3H, s, CH3), 4.35 (2H, t, J 7, OCH2), 7.34 (1H, d, J 8, Ph), 7.65 (1H, d, J 8, Ph), 7.83 (1H, s, Ph); m/z (ES+) 290 (MH+).

المصدر