Ammonium formate → 2-Amino-4-(4,5-dihydro-1h-imidazol-2-yl)phenol

Participants

Reaction Steps

A mixture of the cyclic amidine 35 (490 mg, 2.36 mmol), ammonium formate (1.5 g, 23.6 mmol) and 10% Pd on carbon (50 mg) in methanol was heated at reflux for 4 hrs. After cooling to room temperature, the catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo. The residue was triturated with hexane and the resulting solid was collected to yield 309 mg (74%) of the desired product 37. 1H NMR (600 MHz, DMSO-d6) δ 7.07 (d, 1H, J=1.8 Hz), 6.94 (dd, 1H, J=7.8, 1.8 Hz), 6.64 (d, 1H, J=7.8 Hz), 5.46 (br s, 2H), 4.69 (br s, 1H), 2.64 (s, 4H). MS: m/z Calcd 177.2 Found MH+ 173.3

Provenance & Evidence