N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine → N4-(3-(tert-Butyldimethylsilyloxy)propyl)quinoline-3,4-diamine

Participants

Reaction Steps

Iron powder (10 g) was added to a solution of the product from step (ii) (20 g) in acetic acid (200 mL) and MeOH (100 mL). The mixture was stirred at rt for 30 min then evaporated under reduced pressure. The residue was partitioned between DCM and water, the organics separated, washed with aq NaHCO3 solution, water, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 3-5% MeOH in DCM to give a brown oil, 10.1 g.

Provenance & Evidence