N-(2-benzoylphenyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydroxide (5 M, 1.8 g, 43.9 mmol) was added to a mixture of 2-acetamidobenzophenone (10.5 g, 43.9 mmol) in ethanol (439 mL). The mixture was heated to reflux for 3 hours, then cooled to room temperature and concentrated. Water and methylene chloride were added while stirring to form a white precipitate. The solid was collected by vacuum filtration and washed with methylene chloride to yield 2-hydroxy-4-phenylquinoline. The mixture was heated to reflux for 3 hours concentrated Water and methylene chloride were added to form a white precipitate The solid was collected by vacuum filtration washed with methylene chloride

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloro-4-phenylquinoline was prepared by the following method (Rxn-1). 2-Aminobenzophenone (21 g, 106.5 mmol) was dissolved in methylene chloride (213 mL) and triethylamine (22.3 mL, 159.8 mmol) was added slowly. After cooling to 0° C., acetylchloride (8.3 mL, 117.2 mmol) was added to the reaction mixture dropwise. The reaction mixture was then removed from ice and allowed to stir overnight. Upon the addition of 10% hydrochloric acid (84 mL), the aqueous layers were combined and extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulfate, and concentrated. Purification by column chromatography (25% ethyl acetate/heptane) gave 2-acetamidobenzophenone. The reaction mixture was then removed from ice Upon the addition of 10% hydrochloric acid (84 mL) extracted with ethyl acetate dried with magnesium sulfate concentrated Purification by column chromatography (25% ethyl acetate/heptane)