6-Amino-4-trifluoromethylquinolin-2(1H)-one

Uses

6-Amino-4-(trifluoromethyl)-2(1H)-quinolinone is an intermediate in the synthesis of LGD-2226 (L397615), an orally active potent and selective androgen receptor modulator used in the treatment of muscle wasting and osteoporosis. Show to have an anabolic effect on muscle and bone tissue.

Synthesis

6-Amino-4-trifluoromethylquinolin-2(1H)-one is obtained by reacting Nitro-compound with hydrogen in the presence of 5% Pd/C.
Experimental Procedure：A suspension of the 17.0 g 6-Nitro-4-trifluoromethylquinolin-2(1H)-one in 400 ml ethanol in a 1 L round flask was flushed with argon and 2.0 g 5% Pd/C was added. The mixture was stirred under a hydrogen atmosphere for 2 days. Then filtered through silica and washed with 1500 mL ethanol. The filtrate was evaporated under vacuum to yield 14.0 g of a bright yellow solid 6-Amino-4-trifluoromethylquinolin-2(1H)-one (92%).