4-Toluenesulfonyl chloride → 6-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of the compound of step 4 above (1.4 g), triethylamine (1 ml) and TsCl (1.1 g) in CH2Cl2 is stirred at 25° C. for three days. The mixture is washed with saturated aqueous NaHCO3 and evaporated affording a residue which is dissolved in toluene and refluxed for 21/2 hours. The toluene is evaporated and the residue is dissolved in CH2Cl2 and washed with saturated NaHCO3 (25 mls). The organic layer is dried, evaporated and the residue chromatographed on silica gel affording a gum which crystallizes from HexEt2O to give the desired product (M.P. 105°-108° C.).

Provenance & Evidence