Ammonium formate → HCID 135493010, compound

Participants

Reaction Steps

The 2-(4-benzyloxyphenyl)-3-(4-methoxyphenyl)-6-methylpyridine (14 g, .37 mmol) and ammonium formate (3.5 g, 55 mmol) were stirred in 1 L of EtOH, then 5% Pd/ C (5.8 g, 3 mmol Pd) was added and the reaction mixture warmed to 50°-55° C. The reaction mixture was stirred at 55° C. for 1 h at which time the TLC (MeOH/ CHCl3, 1:9) indicated the starting material was consumed. After cooling, the reaction mixture was filtered, concentrated, and the residue triturated with Et2O to give 9.6 g (90% yield) of white solid: mp 190° C.; 1H NMR (CDCl3) d 2.66 (s, 3H, Pyr-CH3), 3.82 (s, 3H, OCH3), 6.53-6.56 (d, 2H, J=8 Hz, ArH), 6.80-6.83 (d, 2H, J=8 Hz, ArH), 7.06-7.18 (m, 6H, ArH, ArOH), 7.59-7.62 (d, 1H, J=8 Hz, ArH); MS(FD) 291(M+). Anal. Calcd for C19H17NO2 : C, 78.33; H, 5.88; N, 4.81. Found: C, 78.11; H, 5.93; N, 4.72.

Provenance & Evidence