Sodium Hydroxide → HCID 20063315, compound

Participants

Reaction Steps

A solution of ethyl (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)-hept-6-enoate (0.35 g; prepared as described in Example 1) in methanol (15 ml) was cooled to 10° C. and treated with a solution of sodium hydroxide (0.17 g) in water (10 ml) dropwise during 10 minutes. The reaction mixture was warmed to room temperature, stirred for one hour and evaporated to dryness, and the residual solid, which was crude sodium (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)hept-6-enoate, was dissolved in water (50 ml). The aqueous solution was washed with diethyl ether (20 ml) and acidified to pH 5 by treatment with glacial acetic acid. The resulting yellow solid was filtered off and washed well with water, to give (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)hept-6-enoic acid (0.10 g), m.p. 170° C. [Elemental analysis: C, 70.0; H, 5.92; N, 3.37%; calculated: C, 70.2; H, 5.89; N, 3.56%].

Provenance & Evidence