Acetonitrile → 4-Phenylquinolin-2-amine

Reaction equation

[OH-].[K+].[NH2:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O.[C:18](#[N:20])[CH3:19]>>[C:8]1([C:6]2[C:5]3[C:4](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:3]=[C:18]([NH2:20])[CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 3

HCID 6342Acetonitrile2×

HCID 14797Potassium Hydroxide

HCID 760802-Aminobenzophenone

Product 1

HCID 6722654-Phenylquinolin-2-amine

Procedure

Acetonitrile (150 mL) was heated to reflux for 30 minutes in the presence of potassium hydroxide (14.2 g, 254 mmol). 2-amino-benzophenone (10.0 g, 50.7 mmol) in acetonitrile (165 mL) was added to the reaction mixture. After heating to reflux overnight, the mixture was cooled to room temperature, and the resulting solid was filtered. HCl (1.0 M, 100 mL) was added to the solution, and the resulting solid was filtered. The solids were combined, dissolved in ethyl acetate, dried over magnesium sulfate, and filtered. The volatile components were removed with a rotary evaporator, and the solid was recrystallized from ethyl acetate and heptane.