3-Chloroaniline → 7-Chloro-4-methylquinoline

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CO[CH2:11][CH2:12][C:13](OC)(OC)[CH3:14]>[Cl-].[Zn+2].[Cl-].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:6]([C:13]([CH3:14])=[CH:12][CH:11]=[N:5]2)=[CH:7][CH:8]=1

Participants

Procedure

To a mixture containing 3-chloroaniline (1.59 g), ferric chloride hexahydrate (5.4 g), zinc chloride (0.2 g), ethanol (20 ml of 95% aqueous solution) preheated to 60° C. was added 1,3,3-trimethoxybutane (1.48 g). The resulting mixture was refluxed for two hours and allowed to stand overnight. The volatile matrials were then removed in vacuo and the residue rendered basic with 10% aqueous sodium hydroxide. The resulting mixture was partitioned between water and diethyl ether (3 times). The combined ether layer was dried over magnesium sulfate. Rotary evaporation of the ether solution gave a dark liquid. The liquid was added to a silica gel column and eluted with hexane/ethyl acetate (3:1) to give the desired product as tan crystals.