1,2-Dichloroethane → 7-(Benzyloxy)-5-(chloroacetyl)quinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

5-acetyl-7-benzyloxy-1H-quinolin-2-one (7.0 g, 23.86 mmol) is dissolved in a mixture of 1,2-dichloroethane (147 mL), glacial acetic acid (43 mL) and water (7 mL) and combined with N-benzyl-trimethylammonium-dichloriodate (19.0 g, 54.58 mmol). The mixture is stirred for 4.5 hours at 65° C., then diluted with sodium bicarbonate solution and 5% sodium bisulphite solution and stirred for 5 minutes. The precipitate formed is filtered off, washed with water (2×20 mL) and dried in the oven. Yield: 6.0 g (77%); mass spectroscopy: [M+H]+=328.

Provenance & Evidence