4-Isobutylamino-3-nitroquinoline → N4-(2-methylpropyl)quinoline-3,4-diamine

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Reaction Steps

4-Isobutylamino-3-nitroquinoline (31.5 g, 0.1284 moles) from Step (A) above, was dissolved in 300 ml of toluene, and about one g of platinum on charcoal was added thereto. The resulting mixture was hydrogenated on a Parr apparatus for one and one-half hours. The mixture was then heated and filtered. Toluene was removed from the filtrate by rotary evaporation to provide 27.8 g of crude 3-amino-4-(isobutylamino)quinoline. Recrystallization twice from ethyl acetate/hexane provided 18.8 g of purified product, m.p. 98°-100° C. Analysis: Calculated for C13H17N3 : % C, 72.5; % H, 8.0; % N, 19.5; Found: % C, 73.2; % H, 7.8; % N, 19.7.

Provenance & Evidence