반응 #417955

반응 방정식

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

수율 25.0%

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

수율 25.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타The pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   세척This solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   건조dried (MgSO4)
5. 5
   기타the solvent removed in vacuo
6. 6
   기타to afford a pale orange oily solid
7. 7
   기타Recrystallisation from hexane

실험 절차

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+).

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