Sodium borohydride → [2,2'-Bipyridine]-4,4'-diamine

Participants

Reaction Conditions

Reaction Steps

1.34 g of 4,4′-dinitro-2,2′-bipyridine-1,1′-dioxide was suspended in 75 mL of methanol under argon. The mixture was cooled to 0° C. then 0.5 g of 5% Pd/C was added followed by portion wise addition of 1.82 g of sodium borohydride over 10 minutes. The mixture was allowed to warm to room temperature then stirred for 48 hours. The mixture was filtered through a two inch plug of Celite.® Rotary evaporation of the filtrate yielded an off-white solid that was dissolved in 100 mL of 20% HCl. Insoluble residue was removed by filtration then the solution was washed with 100 mL of ether followed by neutralization to pH=8 using 50% NaOH. Cooling to 4° C. yielded a white precipitate which was collected by filtration. The solid was dried under vacuum overnight to yield the desired product as a white powder.

Provenance & Evidence