Reaktion #417955

Reaktionsgleichung

2-amino-5-methylbenzoic acid

octyl chloroformate

→

desired product

Ausbeute 25.0%

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

Ausbeute 25.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe pyridine was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate (50 ml)
3. 3
   WaschenThis solution was washed with 1M HCl (10 ml) and brine (5 ml)
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigethe solvent removed in vacuo
6. 6
   Sonstigeto afford a pale orange oily solid
7. 7
   SonstigeRecrystallisation from hexane

Vorschrift

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+).

Quelle