Stannous chloride dihydrate → 6-bromo-7-chloro-3,4-dihydroquinoxalin-2(1H)-one

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Reaction Steps

A solution of N-(5-bromo-4-chloro-2-nitrophenyl)glycine (0.255 g, 0.824 mmol) and tin (II) chloride dihydrate (0.560 g, 2.48 Aldrich, used as received) was refluxed for 3 h. It was then cooled to r.t. and allowed to stand overnight at r.t. The whim solid was filtered and dried to yield 0.038 g (18%) of pure title compound as white flakes; m.p. 230°-232° C.; 1H NMR (DMSO-d6): 3.732 (s, 2H), 6.371 (s, 1H), 6.830 (s, 1H), 6.912 (s, 1H), 10.437 (s, 1H). Extraction of the filtrate with ethyl acetate (30 mL) gave 0.136 g (68%) more product to get a combined yield of 81%.

Provenance & Evidence