Reaction #1876816

Reaction equation

acetylchloride

2-Aminobenzophenone

triethylamine

→

2-Chloro-4-phenylquinoline

2-acetamidobenzophenone

Solvents

methylene chloride

Conditions

Workup

1. 1
   OtherThe reaction mixture was then removed from ice
2. 2
   workup.ADDITIONUpon the addition of 10% hydrochloric acid (84 mL)
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Dryingdried with magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   OtherPurification by column chromatography (25% ethyl acetate/heptane)

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.

Source