反应 #417955

反应方程式

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

收率 25.0%

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

收率 25.0%

溶剂

pyridine

反应条件

后处理

1. 1
   其他The pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   洗涤This solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   干燥dried (MgSO4)
5. 5
   其他the solvent removed in vacuo
6. 6
   其他to afford a pale orange oily solid
7. 7
   其他Recrystallisation from hexane

实验过程

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+).

来源