N-quinolin-8-ylquinolin-6-amine → HCID 58899096, compound

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Reaction Steps

A solution of 3.68 grams of N-quinolin-8-ylquinolin-6-amine from above in 60 mL of acetic acid containing 0.22 grams of platinum(IV) oxide was hydrogenated at 40 psi for 2.0 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 1.6 grams of brown solid. The solid was chromatographed on silica gel, eluting with hexane/ethyl acetate gradient to afford 0.8 grams of the desired product as a purple solid. 1H NMR (CDCl3/D2O) δ 6.4-6.9 (m, 6H), 3.2-3.4 (m, 4H), 2.6-2.9 (m, 4H), 1.8-2.1 (m, 4H).

Provenance & Evidence