Diisobutylaluminum hydride → [2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To 50 g of methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate added toluene (250 ml) and stirred for 15 minutes at 25° C. Cooled the reaction mixture to 0° C. Added 300 ml of DIBAL H (25% solution in toluene) to the reaction mixture slowly in 45 minutes at the same temperature. Stirred the reaction mixture for 1 hr at 0° C. Quenched the reaction mixture with HCl (110 ml) solution at 10° C. and stirred for 15 minutes. Raised the temperature to 25° C. and stirred for 30 minutes. Separated the both aqueous and organic layers. Extracted the aqueous layer with toluene (400 ml). Adjusted the pH of the reaction mixture with 10% sodium bicarbonate solution (200 ml). Washed the organic layer with saturated sodium chloride solution (200 ml). Distilled off the solvent completely to obtain a solid. Added cyclohexane (50 ml) to the solid and distilled it. To the residue added cyclohexane (150 ml) and stir for 30 minutes at 45° C. Cooled the reaction mixture to 25° C. and stirred for 1 hr. at the same temperature. Filtered the cake, washed with cyclohexane (50 ml) and then dried to get the title compound.

Provenance & Evidence