Acetic Acid → 8-Amino-5-decoxy-6-methoxyquinoline

Participants

Reaction Steps

A stirred mixture of 4.7 g (0.013 mole) of 5-decoxy-6-methoxy-8-nitroquinoline, 12 g of degreased 40 mesh iron filings, 6 ml of butyl ether, 6 ml of acetic acid and 30 ml of water was heated at 100° for 2 hr, cooled and filtered. The solid was washed with water, dried and extracted with diethyl ether. Evaporation of the diethyl ether, solution of the residue in petroleum ether (20°-40°) and cooling in Dry-Ice acetone gave 3.6 g of pale green solid. Two crystallizations from petroleum ether (20°-40°) (carbon) provided 2.3 g (54%) of amino compound as yellow-green solid, mp 65°.

Provenance & Evidence