Hydroxylamine → N'-hydroxy-6-(hydroxymethyl)nicotinimidamide
Reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1.[NH2:11][OH:12]>C(O)C>[OH:12][N:11]=[C:7]([NH2:8])[C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[N:4][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-(hydroxymethyl)nicotinonitrile (ChemPacific, 0.698 g; 5.2 mmol) and 50% aqueous hydroxylamine (1.6 mL) in ethanol (10 mL) was heated at 80° C. for 3 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was passed through a hydrophobic frit and evaporated in vacuo. The resultant solid was washed with MeCN and dried to afford the title product (0.850 g, 98%). 1H NMR (DMSO-d6, 400 MHz) δ 9.79 (1 H, s), 8.79 (1 H, d, J=2.2 Hz), 8.05 (1 H, dd, J=8.2, 2.3 Hz), 7.49 (1 H, d, J=8.2 Hz), 5.98 (2 H, s), 5.56-5.40 (1 H, m), 4.60 (2 H, d, J=4.8 Hz).