Reacción #417955

Ecuación de reacción

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

Rendimiento 25.0%

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

Rendimiento 25.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   LavadoThis solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   Secadodried (MgSO4)
5. 5
   Otrothe solvent removed in vacuo
6. 6
   Otroto afford a pale orange oily solid
7. 7
   OtroRecrystallisation from hexane

Procedimiento

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+).

Fuente