Methanol → HCID 22614878, compound

Participants

Reaction Steps

A 25% w/w solution of sodium methoxide in methanol (433 μL, 1.89 mmol) was added dropwise to a solution of the above mixture of 5-amino-2,3,7-trichloro-6-methylquinoxaline and 5-amino-2,3,6-trichloro-7-methylquinoxaline (200 mg, 0.788 mmol) in dry tetrahydrofuran (7.9 mL) at 0° C. under nitrogen. The mixture was stirred for 3 hours, diluted with ethyl acetate (30 mL), washed with water (2×10 mL), brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The solid residue was purified by flash chromatography on silica gel, by gradient elution using hexane:ethyl acetate (95:5 changing to 1:1, by volume) to give as the first eluted isomer, 5-amino-6-chloro-2,3-dimethoxy-7-methylquinoxaline (48 mg, 25%) as an off-white solid, mp 169-170° C.

Provenance & Evidence