Hydroxyamine hydrochloride → HCID 178436634, compound

Participants

Reaction Steps

To an ice-cooled solution of potassium tert.-butylate (7.11 g, 63.4 mmol) in methanol (50 mL), hydroxylamine hydrochloride (3.78 g, 54.4 mmol) is added. The suspension is stirred for 30 min before 2-ethyl-4-cyano-6-methyl-pyridine (2.65 g, 18.1 mmol) is added. The mixture is refluxed for 3 h before it is filtered. The filtrate is evaporated to dryness and the resulting solid is dissolved in water (30 mL) and extracted with EA (3×150 mL). The combined org. extracts are concentrated and dried under HV to give 2-ethyl-N-hydroxy-6-methyl-isonicotinamidine (3.43 g) as a white powder; LC-MS: tR=0.31 min, [M+1]+=180.07; 1H NMR (D6-DMSO) δ 1.22 (t, J=7.5 Hz, 3H), 2.44 (s, 3H), 2.71 (q, J=7.5 Hz, 2H), 5.89 (s, 2H), 7.31 (s, 2H), 9.87 (m, 1H).

Provenance & Evidence