Acetic Acid → HCID 11150264, compound

Participants

Reaction Steps

A solution of the methyl 2-sodio-2(4′-methoxybenzoyl) acetate salt prepared in Example 1(44.60 g, 0.194 mol) and 4-toluidine (20.85 g, 0.195 mol) in xylene (300 ml) was stirred and heated over 1 hour. Glacial acetic acid (11.7 g, 0.195 mol) in xylene (100 ml) was added which caused the mixture to become viscous. The mixture was then heated at reflux for 6 hours and allowed to cool to room temperature. Xylene (200 ml) was added to reduce the viscosity of the mixture. This solution was heated at reflux for 4 hours and allowed to cool to room temperature. The solid N-(4′-methoxybenzoylacetyl)-4-methylaniline product obtained was collected by filtration and washed with toluene and heptane. After removal of the residual organic solvent by drying, the solid product was re-suspended with water (250 ml) and stirred. The solid product was collected by filtration and dried (7.13 g, 13%); m.p. 122-126° C. The solvent was removed from the filtrate. The residue crystallized upon standing and was recrystallized in ethanol to give an additional purified solid product (6.83 g, 12 wt. %); m.p. 127-130° C.

Provenance & Evidence