3-Chloropropiophenone → HCID 21837483, compound

Participants

Reaction Steps

HCl/diethyl ether (30.8 ml) was added to a solution of 4-amino-4'-chlorobenzophenone (35 g) in ethanol (250 ml) at room temperature and the mixture was stirred for 15 minutes. FeCl3.6H2O (69.4 g) and then ZnCl2 (2.05 g) were added portionwise and the mixture was stirred at 65° C. for 30 minutes. 3-Chloro-1-phenyl-1-propanone (25.46 g) was added and the mixture was stirred and refluxed for one night. The mixture was poured into ice and extracted with DCM. The organic layer was washed with K2CO3 10%, dried (MgSO4), filtered off and evaporated. The residue was crystallized from ACN. The mother layers were purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 99/1). The pure fractions were collected and evaporated, yielding 19.4 g (37%) of (4-chlorophenyl)(4-phenyl-6-quinolinyl)methanone (interm. 8-a).

Provenance & Evidence