Methanol → 7-hydroxymethyl-1-isopropyl-4-phenyl-2(1H)-quinazolinone

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Reaction Steps

A mixture of 69.3 of crude 7-bromomethyl-1-isopropyl-4-phenyl-2(1H)-quinazolinone (obtained by repeating Step A, above), 500 ml of a 10% aqueous sodium carbonate solution and 500 ml of methanol is refluxed for 8 hours, cooled, diluted by addition of 200 ml of distilled water containing 6 ml of 10N sodium hydroxide solution, and the resulting mixture extracted 3 times each with 400 ml of chloroform. Each extract is then washed twice with 200 ml portions of distilled water. The organic extracts are combined and evaporated to dryness to obtain a residue. The residue, thus obtained, is taken up in 100 ml of a mixture of chloroform: benzene (1:1), which solution is then placed on a chromatographic column of 480 g of silica gel in the same solvent. The column is eluted and fractions of from about 600 to 750 ml taken, in turn with 3 liters of chloroform: benzene (1:1) (fractions 1 to 4); 2 liters of 100% chloroform (fractions 5 to 7); 5 liters of ethyl acetate: chloroform (1:3) (fractions 8 to 14); and lastly 3 liters of ethyl acetate: Chloroform (1:1) (fractions 15 to 18). Fractions 9 to 14 are combined and evaporated to dryness to obtain a residue which yields refined title compound on repeated crystallization from ethyl acetate, m.p. 223° -225°.

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