Ammonium formate → HCID 10705894, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium formate (3.5 g, 48 mmol) was added to a solution of (37) (1.8 g, 4.8 mmol) in 60 mL of absolute ethanol. The mixture was purged with argon then palladium (0.5 g, 5% on activated carbon) was added. The resulting mixture was heated at 80° C. for with argon then palladium (0.5 g, 5% on activated carbon) was added. The resulting mixture was heated at 80° C. for 12 h then was cooled to 25° C. and filtered through celite. The filtrate was concentrated in vacuo and the residue was cooled to 0° C. Saturated Na2CO3 (100 mL) was added, and the resulting mixture was stirred for 30 min. The aqueous layer was extracted with EtOAc (3×50 mL) and the combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give 1.3 g (quantitative yield) of the title compound: TLC (Rf =0.24; 10% MeOH/CH2Cl2); 1H NMR (DMSO) δ 7.86 (d, 1H, J=6.9), 7.28 (s, 1H), 7.10 (br s, 2H), 3.95 (m, 1H), 3.69 (s, 3H), 3.26 (d, 2H, J=12.8), 2.92 (t, 2H, J=9.8), 2.00 (d, 2H, J=12.0), 1.70 (m, 2H); 13C NMR (DMSO) δ 167.0, 156.4, 154.6, 122.8, 109.8, 50.9, 44.4, 41.8, 27.9; HRMS (FAB) m/z 252.1466 (M+H)+ (C11H17N5O2 requires 252.1461).

Provenance & Evidence