Ethyl Acetate → HCID 136207703, compound

Participants

Reaction Steps

The 2-(4-benzyloxyphenyl)-3,6-bis(4-methoxyphenyl)pyridine (3.0 g, 6.3 mmol), ammonium formate (2.0 g, 31 mmol), and 5% Pd/C (1.0 g, 0.5 mmol Pd) were combined in 150 mL of EtOH, and the reaction mixture was stirred at 50°-55 ° C. and followed by TLC (EtOAc/ Tol, 1:9). After 1 h, more ammonium formate (0.5 g, 8 mmol) was added and reaction mixture stirred at 50° C. for 30 min and no starting material remained. After cooling, the reaction mixture was filtered, concentrated, and the residue triturated with Et2O/ pet. ether. The white ppt was filtered and dried in vacuo to give 2.35g (97% yield) of product: mp 204°-205° C.; 1H NMR (CDCl3) d 3.83 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 4.85 (s, 1H, ArOH), 6.71-6.74 (d, 2H, J=9 Hz, ArH), 6.83-6.86 (d, 2H, J=9 Hz, ArH), 7.00-7.03 (d, 2H, J=9 Hz, ArH), 7.14-7.17 (d, 2H, J=9 Hz, ArH), 7.37-7.40 (d, 2H, J=9 Hz, ArH), 7.68-7.70 (m, 2H, ArH), 8.08-8.11 (d, 2H, J=9 Hz, ArH); MS(FD) 383(M+). Anal. Calcd for C25H21NO3 : C, 78.31; H, 5.52; N, 3.65. Found: C, 78.07; H, 5.79; N, 3.95.

Provenance & Evidence