Quinoline → HCID 53723341, compound

Participants

Reaction Steps

A solution of 20-hydroxymethyl-4-nitropregn-4-en-3-one (2.01 g, 5.35 mM) in absolute ethanol (28 mL) is treated sequentially with Lindlar's catalyst (5% Pd on CaCO3 with 5.2% Pb, 0.81 g) and with quinoline (37) and kept under hydrogen at between 40-55 p.s.i. for 24 hours. The mixture is then filtered through celite, and the filtrate is concentrated to a yellow solid which is purified by short path chromatography to give 4-amino-20-hydroxymethylpregn- 4-en-3-one, m.p. 180°-185° C. (aqueous isopropanol). IR 3512, 3470, 3384, 1648, 1614, 1576 cm-1 MS(CI) 346(100%, M+1), 328(30%, M+l-H2O).

Provenance & Evidence