Water → HCID 13577662, compound

Participants

Reaction Steps

To a slurry of 5.5 g (0.145 mole) of lithium aluminum hydride in 50 ml of dry tetrahydrofuran was added dropwise a solution of 21.9 g (0.069 mole) of 2-amino-3-(4-chlorobenzoyl)benzeneacetic acid, ethyl ester in 120 ml of dry tetrahydrofuran. After the addition was complete, the mixture was heated at reflux under a nitrogen atmosphere for 2.5 hours. The mixture was cooled and treated successively with 5.5 ml of water, 5.5 ml of 5% sodium hydroxide and 16.5 ml of water. The mixture was filtered through celite and the filter cake was washed several times with tetrahydrofuran. The combined filtrates were concentrated to give a solid residue. This residue was recrystallized from ethyl acetate to yield 8.6 g (45%) of the titled compound as fluffy white needles, m.p. 132°-134° C.

Provenance & Evidence