反応 #417955

反応方程式

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

収率 25.0%

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

収率 25.0%

溶媒

pyridine

反応条件

後処理

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

実験手順

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+).

出典