Diphenyl-(5-nitro-2-pyridyl)acetamide → HCID 10902759, compound

Participants

Reaction Steps

A mixture of 8.86 g of diphenyl-(5-nitro-2-pyridyl)acetamide (26.5 mmol) in 50% EtOH/glacial AcOH with 100 mg platinum (IV) oxide was shaken on a Parr hydrogenator (30 psi H2) for 3 hr. The mixture was filtered through a bed of Celite, then the ethanol was evaporated under reduced pressure. The mixture was then basified with K2CO3 and extracted with EtOAc (4×), dried (MgSO4), filtered through Celite again and evaporated. The remaining solid was recrystallized from hexane/EtOAc/MeOH to furnish the title compound (7.9 g, 98%) as a tan crystal. mp 215-20° C. 1H NMR (CDCl3; 300 MHz) δ 3.85 (2H, bs, NH), 5.88 (1H, bs, CONH), 6.54 (1H, d, J=8.4 Hz), 6.84 (1H, dd, J=3 and 8.7 Hz), 7.01 - 7.06 (4H, m), 7.24-7.32 (6H, m), 8.11 (1H, d, J=2.4 Hz, H-6), 9.57 (1H, bs, CONH). Elemental analysis calculated for C19H17N3O 0.25 H2O: C, 74.15; H, 5.69; N, 13.67. Found: C, 74.06; N, 5.69; H, 13.78.

Provenance & Evidence