Hydrochloric Acid → HCID 178470060, compound

Participants

Reaction Steps

A solution of ethyl 3-(5-chloro-2-nitrophenylamino)-3-oxopropanoate (1.5 g, 5.2 mmol) in anhydrous DMF (8 mL) was added dropwise to a solution of potassium tert-butoxide (1.2 g, 10.5 mmol) in anhydrous DMF (5 mL) at 0° C. under nitrogen, after which the mixture was stirred for 2 h. The cold mixture was diluted with water (50 mL), acidified to pH 2 with 2 N HCl and extracted with methylene chloride (3×30 mL). The combined organic extracts were washed with water (45 mL), dried over sodium sulfate, filtered and the solvents were removed under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (3:7), to provide 6-chloro-2-(ethoxycarbonyl)-3-hydroxyquinoxaline-1-oxide as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.25 (d, 1H), 7.46 (d, 1H), 7.34 (dd, 1H), 4.55 (q, 2H), 1.45 (t, 3H) ppm; ESI MS m/z 267 [M−H]−.

Provenance & Evidence