Hydroxyamine hydrochloride → HCID 178426675, compound

Participants

Reaction Steps

To an ice-cooled solution of potassium tert.-butylate (284 g, 2.53 mmol) in methanol (4 mL), hydroxylamine hydrochloride (151 mg, 2.17 mmol) is added. The suspension is stirred for 30 min before 6-isobutyl-5-methyl-nicotinonitrile (126 mg, 0.723 mmol) is added. The mixture is refluxed for 1 h before the solvent is evaporated. The residue is dissolved in sat. aq. NaHCO3-solution (10 mL) and extracted with EA (3×15 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried under HV to give N-hydroxy-6-isobutyl-5-methyl-nicotinamidine (143 mg) as a white solid; LC-MS: tR=0.56 min, [M+1]+=208.13; 1H NMR (CDCl3): δ 0.97 (d, J=6.8 Hz, 6H), 2.16 (hept, J=7.0 Hz, 1H), 2.36 (s, 3H), 2.72 (d, J=7.3 Hz, 2H), 4.91 (s, 2H), 7.70 (d, J=1.3 Hz, 1H), 8.66 (d, J=1.8 Hz, 1H).

Provenance & Evidence