Ammonium formate → HCID 10681198, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium formate (4.2 g, 66 mmol) was added to a solution of 46 (2.3 g, 6.9 mmol) in 100 mL of absolute ethanol. The mixture was purged with argon then palladium (0.8 g, 5% on activated carbon) was added. The resulting mixture was heated to 80° C. and maintained at that temperature for 12 h. After cooling to 25° C., the mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was cooled to 0° C., saturated NaHCO3 (100 mL) was added and the resulting mixture was stirred for 30 min. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give 1.53 g (94%) of the title compound: TLC (Rf =0.20; 15% MeOH/CH2Cl2); 1H NMR (CDCl3) δ 7.85 (d, 2H, J=8.8), 6.54 (d, 2H, J=8.8), 4.08 (d, 1H, J=7.6), 3.85 (s, 3H), 3.47 (m, 1H), 3.13 (d, 2H, J=12.8), 2.72 (t, 2H, J=11.9), 2.07 (d, 2H, J=2.1), 1.37 (m, 2H); 13C NMR (CDCl3) δ 167.3, 150.7, 131.6, 118.0, 111.7, 51.5, 49.9, 45.4, 33.6; Anal. (C13H18N2O2 ·1/4 H2O·1/2 CH3OH) C, H, N.

Provenance & Evidence