Hydrochloric Acid → 5,8-Bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylic acid

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Reaction Steps

A solution containing diethyl 5,8-bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylate 3 (84.7 g, 180 mmol), 5 N NaOH (180 ml), THF (360 ml) and MeOH (180 ml) was heated to 60 C for 1.5 h. This mixture was then added to half-saturated NH4Cl and acidified with 2 N HCl to pH 0-1. The product was extracted into i-PrOAc:THF 1:1, dried over Na2SO4 and concentrated. It was triturated with ether:hexane 1:4 to yield the diacid 4 as an off-white solid (approx 100% yield).

Provenance & Evidence