Water → HCID 67395629, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% dispersion in mineral oil, 12.0 g, 300 mmol) in toluene (450 mL) was added a solution of ethyl 7-fluoro-3-methylquinoxaline 2-carboxylate (35.1 g, 150 mmol) and acetonitrile (19.6 mL, 375 mmol) in toluene (40 mL) dropwise over 35 min at 85° C. After being stirred for 5 min at the same temperature, the reaction mixture was cooled to 0° C., and then added water (175 mL). The aqueous layer was separated and the organic layer was extracted with 1N aqueous sodium hydroxide (200 mL). The combined aqueous layer was acidified to pH 2 with conc. Hydrochloric acid (45.0 mL) at 0° C., and the resulting precipitate was collected and washed with water (150 mL). The solid was dissolved with chloroform (1000 mL) and water (500 mL). The aqueous layer was extracted with chloroform (300 mL). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was triturated with ethanol to give 3-(7-fluoro-3-methylquinoxalin-2-yl)-3-oxopropanenitrile. MS (APCI): m/z 230 (M+H).

Provenance & Evidence