Dihydro-3,3-diethyl-2,5-furandione → 4-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

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Reaction Steps

0.36 g of 3-(7-acetyl-2-quinolinylmethoxy)aniline and 0.385 g of 2,2-diethylsuccinic acid anhydride are stirred in 5 ml of pyridine for 72 hours at 20° and concentrated by evaporation. The residue is suspended in 5 ml of 2N aqueous hydrochloric acid, the suspension is stirred for 30 min. at 20° and filtered and the residue retained on the filter is dried in vacuo at 20°. The crude product obtained is chromatographed on 50 g of silica gel. The product-containing fractions (eluted with toluene/ethyl acetate 1:1 and with ethyl acetate) are combined and concentrated by evaporation and the evaporation residue is recrystallised from a CH2Cl2 /methanol/acetone mixture to give the title compound in the form of crystals of m.p. 164°. IR (Nujol): inter alia 3600-2100, 3350, 1675, 1600 cm-1.

Provenance & Evidence