Hydroxylamine → N-Hydroxy-6-methyl-nicotinamidine

HRID 713760Notes

Reaction equation

HRID 713760 reaction equation
[NH2:1][OH:2].[CH3:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][N:5]=1>C(O)C>[OH:2][N:1]=[C:8]([NH2:9])[C:7]1[CH:10]=[CH:11][C:4]([CH3:3])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 2819956-Methylpyridine-3-carbonitrile

Product 1

HCID 73867086N-Hydroxy-6-methyl-nicotinamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydroxylamine (Aldrich, 0.765 g, 10 mmol) in ethanol (10 mL) was treated with a solution 6-methylnicotinonitrile (Aldrich, 12.8 g, 100 mmol) in ethanol (10 mL). The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed under vacuum and the residue was purified with flash column chromatography (5% methanol/dichloromethane) give the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 2.2 (s, 3H), 6.02 (bs, 2H), 7.59 (m, 1H), 8.06-8.0 (m, 2H), 10.2 (s, 1H) ppm; MS (DCl/NH3) m/z 152 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified with flash column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d0e87a97451340b89cfdcdd5af984e8e
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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