Acetophenone → N-(4-chlorophenyl)-1-phenylethanimine
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>O>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([N:15]=[C:1]([CH3:2])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:13][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of acetophenone (132 ml), p-chloroaniline (128 g) benzene (150 ml) was refluxed in the presence of molecular sieve (40 g) with continuous removal of water. The crude product was crystallized from ethanol to give p-chloro-N-(α-methyl benzylidene) aniline (XVII). It was then hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent. The crude product was crystallized from ethanol and pet. ether to give p-chloro-N-(α-methyl benzyl) aniline (XVIII). XVIII had a melting point of 62° C.