7-(benzyloxy)-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitroquinolin-4-amine → HCID 66649879, compound

Participants

Reaction Steps

A 3-liter stainless steel Parr vessel was charged sequentially with 5% platinum on carbon catalyst, acetonitrile (250 mL), 7-(benzyloxy)-N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitroquinolin-4-amine (102 g, 0.225 mol), and additional acetonitrile (1250 mL). The vessel was evacuated and charged with hydrogen gas (30 psi, 2.1×105 Pa). The vessel was shaken overnight. The reaction mixture was then filtered through a layer of CELITE filter agent. The filter cake was rinsed with additional acetonitrile (2 L), and the combined filtrates were concentrated under reduced pressure to provide 95 g of 7-(benzyloxy)-N4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)quinoline-3,4-diamine as an orange-green solid.

Provenance & Evidence