Sodium borohydride → tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

Participants

Reaction Conditions

Reaction Steps

Nickel(II) chloride hexahydrate (18.4 g) was dissolved in MeOH (360 mL) and cooled to 5° C. Sodium borohydride (2.9 g) was added followed by the product from step (i) (28 g). More sodium borohydride (11.7 g) was added slowly keeping the temperature below 23° C. then stirred for 1 h. The reaction mixture was filtered through celite and the filtrate was poured into sodium bicarbonate solution (300 mL). The solvent was reduced by half and then extracted with chloroform, combined organics were dried, and solvent removed to give the subtitle compound as a solid (22 g); MS multimode (+) 331

Provenance & Evidence