HCID 58899098, compound → HCID 57589732, compound

Participants

Reaction Steps

A solution of 2.46 grams of N-(4-tert-butylphenyl)quinolin-8-amine from Step A in 100 mL of acetic acid containing 0.15 grams of platinum(IV) oxide was hydrogenated at 45 psi for 1.5 hours on a Parr low-pressure hydrogenator. The solution was filtered through diatomaceous earth; concentrated in vacuo; and neutralized with 3N aqueous sodium hydroxide. The aqueous phase was diluted with water and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with brine; dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 2.5 grams of dark blue oil. The oil was chromatographed on silica gel, eluting with hexane/ethyl acetate (20:1) to afford 2.0 grams of the desired product as a yellow oil. 1H NMR (CDCl3) δ 7.2 (d, 2H), 6.5-6.95 (m, 5H), 4.95 (bs, 1H), 3.3 (t, 2H), 2.8 (t, 2H), 1.9 (p, 2H), 1.3 (s, 9H).

Provenance & Evidence