Toluene → N4-Isobutyl-1,5-naphthyridine-3,4-diamine

Participants

Reaction Conditions

Reaction Steps

A hydrogenation vessel was charged with N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (7.50 kg, 30.5 mol) and toluene (125.0 kg). A suspension of 3% platinum on carbon (0.44 kg, approximately 33% by weight (w/w) in water) in isopropanol (7.0 kg) was added to the vessel followed by a rinse with toluene (10.0 kg). The reaction mixture was then placed under hydrogen pressure (2.4×105 Pa, 2.4 bars) for six hours while stirring and maintaining the temperature at 22° C. The reaction mixture was then filtered, and the filter cake was washed with toluene (30.0 kg). The filtrate was concentrated under reduced pressure (1×104 Pa, 0.1 bar) at approximately 50° C. to provide a solution of N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine in toluene (75 L, approximately 10 mL/g).

Provenance & Evidence