Benzyl acetone → HCID 22163833, compound

Participants

Reaction Conditions

Reaction Steps

An oily suspension (50% by weight; 4.7 g) of sodium hydride is added at a temperature in the region of 0° C. to a solution, maintained under a nitrogen atmosphere, of 3-hydroxy-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (15 g) in anhydrous dimethylformamide (280 cc), and the suspension obtained is stirred for 30 minutes at a temperature in the region of 0° C. A solution of benzylacetone (14.4 g) in anhydrous dimethylformamide (20 cc) is added and stirring is continued for 21 hours at a temperature in the region of 0° C. The reaction mixture is then poured into distilled water (1.5 litres). The pH of the aqueous phase is brought to approximately 5 by adding 4 N aqueous hydrochloric acid solution. The product i$ extracted with methylene chloride (3×500 cc). The organic phases are combined and washed with distilled water (3×80 cc), dried over magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (2.7 kPa). The oily residue obtained is purified by chromatography under pressure (50 kPa) on silica gel (0.040-0.063 mm; 200 g) contained in a column 2.8 cm in diameter. Elution is performed with methylene chloride, collecting 50-cc fractions. Fractions 9 to 21 are combined and concentrated to dryness at 40° C. under reduced pressure (2.7 kPa). After the solid obtained is recrystallized in ethanol, 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-(2-oxo-4-phenylbutyl)-1-isoindolinone (3.4 g), m.p. 180° C., is obtained.

Provenance & Evidence