Oxalic Acid → HCID 20065673, compound

Participants

Reaction Steps

A solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1pyridyl)propyl]-3-hydroxy-1-isoindolinone (8 g) in anhydrous dimethylformamide (75 cc) is added to a suspension of sodium hydride (as a 50% suspension in oil) (1.2 g) in anhydrous dimethylformamide (15 cc) at a temperature close to 20° C. in the course of 15 minutes and agitation is continued for 3 hours. Then, 2.6 g of butyryl chloride is added in the course of 10 minutes, and agitation is continued for a further 20 hours. The suspension obtained is poured into distilled water (400 cc) and extracted with methylene chloride (4×200 cc). The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in acetonitrile (120 cc). A solution of oxalic acid (2.3 g) in acetonitrile (60 cc) is added and agitation continued for 1 hour at a temperature close to 20° C. The precipitate formed is separated by filtration. 8.1 g of 3-butyryloxy-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone oxalate are thus obtained, melting at 160° C.

Provenance & Evidence