3-(4-Chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde → HCID 68705972, compound

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Reaction Steps

A stirred mixture of 3-(4-chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde (0.063 g, 0.158 mmol) in 1M HCl solution (4 ml) and methanol (6 ml) is heated under reflux for 1 h under a nitrogen atmosphere. The mixture is allowed to cool to room temperature, and the methanol solvent is removed by evaporation in vacuo. The concentrated mixture is diluted with water (5 ml) and treated with solid sodium hydrogen carbonate, until a pH of 7-8 is attained. The mixture is washed successively with ethyl acetate and methylene chloride. The combined organic phases are dried (magnesium sulfate) and filtered, and the solvent is removed by evaporation in vacuo to afford a crude orange solid. This is stirred overnight in a solution of 2M HCl in diethyl ether (3 ml), filtered and dried at room temperature under high vacuum to give the title compound as a cream-coloured solid.

Provenance & Evidence