2-(Chloromethyl)anisole → HCID 10907363, compound

Participants

Reaction Steps

A 50% solution of 1.8 g of 2-methoxybenzyl chloride ("A") in dichloromethane is added to a solution of 2.0 g of ethyl 4-(1,4-benzodioxan-6-yl)-1,2-dihydro-2-oxobenzofuro[3,2-b]pyridine-3-carboxylate (obtainable by reaction of 3-amino-2-(1,4-benzodioxan-6-carbonyl)benzofuran and diethyl malonate in acetone and potassium carbonate, m.p. 255°; 3-amino-2-(1,4-benzodioxan-6-carbonyl)benzofuran is obtainable by reaction of 2-hydroxybenzonitrile and 6-bromoacetyl-1,4-benzodioxane, m.p. 157°) in 15 ml of DMF and 2.5 g of caesium carbonate. The reaction mixture is stirred for 10 hours and worked up in the customary manner. The N-alkylation product ethyl 4-(1,4-benzodioxan-6-yl)-1,2-dihydro-1-(2-methoxybenzyl)-2-oxobenzofuro[3,2-b]pyridine-3-carboxylate, m.p. 105° and the O-alkylation product ethyl 4-(1,4-benzodioxan-6-yl)-2-(2-methoxybenzyloxy)benzofuro[3,2-b]pyridine-3-carboxylate, m.p. 166°, are obtained.

Provenance & Evidence