Reacción #47953

Ecuación de reacción

EDC

diisopropylethylamine

O,N-dimethyl-hydroxylamine hydrochloride

2-amino-5-fluorobenzoic acid

→

2-amino-5-fluoro-N-methoxy-N-methylbenzamide

Disolventes

CHCl3

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL)
2. 2
   Secadodried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroPurification by normal phase chromatography (3-8% MeOH/CH2Cl2)

Procedimiento

To a 0° C. mixture of diisopropylethylamine (34.36 mL, 197.25 mmol) and O,N-dimethyl-hydroxylamine hydrochloride (19.24 g, 197.25 mmol) in CHCl3 (300 mL) was added 2-amino-5-fluorobenzoic acid (25.50 g, 164.38 mmol) followed by EDC (31.51 g, 164.38 mmol). The reaction was stirred from 0° C. to ambient temperature over 2 h and then diluted with CH2Cl2 (100 mL), washed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase chromatography (3-8% MeOH/CH2Cl2) yielded 2-amino-5-fluoro-N-methoxy-N-methylbenzamide as a yellow oil. 1H NMR (CDCl3, 400 MHz) 7.12 (m, 1H, ArH); 6.93 (m, 1H, ArH); 6.65 (m, 1H, ArH); 3.63 (s, 3H, CH3); 3.35 (s, 3H, CH3); MS (Electrospray): m/z 199.1 (M+H).

Fuente