Lithium Hydroxide → Quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[6-(1-methanesulfonyl-1-methylethyl)-quinolin-8-yl]-benzoic acid methyl ester from Step 1 (1.0 eq) in THF (20 mL) was added LiOH (2.5 eq; 2.0N in water). The mixture was stirred at 65° C. for 6 h then poured in NaOH (1N) then extracted with CH2Cl2 (2×). The organic extracts were discarded while the aqueous phase was acidified to pH=5 using AcOH. The latter was extracted with CH2Cl2 (5×). The combined organic extracts were dried over MgSO4, filtered and concentrated. The resulting solid was stirred in a mixture of EtOAc:Hex:Et2O (0.1:1:1) then filtered to afforded the title compound as a white solid.

Provenance & Evidence