Ethyl Acetate → 4-[3-(6-Methyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

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Reaction Steps

3-(6-methyl-2-quinolinylmethoxy)aniline: 0.43 g of NaH (95%) is added at 0° to a solution of 1.85 g of 3-aminophenol in 30 ml of DMF and then the batch is stirred for 30 min. at 0°. 3.2 g of 2-chloromethyl-6-methyl-quinoline [see C.A. 82, 57733p and U.S. Pat. No. 3,829,573] in solid form are then added and the batch is stirred for a further one hour at 0° and for another hour at 20°. It is then diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated by evaporation. The evaporation residue is chromatographed on 250 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 95:5 and 9:1 are combined and concentrated by evaporation to give the title compound which is further purified by being crystallised twice from CH2Cl2 /ether/hexane.

Provenance & Evidence