Réaction #417955

Équation de réaction

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

Rendement 25.0%

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

Rendement 25.0%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   AutreThe pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   LavageThis solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   Séchagedried (MgSO4)
5. 5
   Autrethe solvent removed in vacuo
6. 6
   Autreto afford a pale orange oily solid
7. 7
   AutreRecrystallisation from hexane

Mode opératoire

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+).

Source