Reaction #1256754

Reaction equation

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

Yield 25.0%

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

Yield 25.0%

Solvents

pyridine

Conditions

Workup

1. 1
   OtherThe pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   WashThis solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   Dryingdried (MgSO4)
5. 5
   Otherthe solvent removed in vacuo
6. 6
   Otherto afford a pale orange oily solid
7. 7
   OtherRecrystallisation from hexane

Procedure

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