Ammonia → HCID 59004663, compound

Participants

Reaction Steps

A solution of compound 60 (400 mg, 1.4 mmol) in methanol (10 mL) was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was treated with hydrazine hydrate (435 μL, 14.0 mmol) and heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad washed with methanol (10 mL). The filtrate was concentrated to give a dark brown residue which was subjected to flash silica gel chromatography (2M NH3 in MeOH:CH2Cl2, 5:95) to give compound 61 (260 mg, 72.2%) as a viscous oil. 1H NMR (DMSO-d6) δ 7.14 (d, J=3.0 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 6.67 (d, J=1.8 Hz, 1H), 6.52 (dd, J=1.8, 8.7 Hz, 1H), 6.09 (d, J=1.8 Hz, 1H), 4.45 (brs, 2H), 4.04 (t, J=7.2 Hz, 2H), 2.76-2.72 (m, 1H), 2.15 (s, 3H), 2.02-1.17 (m, 10H); ESI-MS (m/z, %): 258 (M+1).

Provenance & Evidence