Hydroxyamine hydrochloride → 5-Methyl-6-methylthio-3-pyridinecarboxamide

HRID 368287Notes

Reaction equation

HRID 368287 reaction equation
C[O-:2].Cl.NO.[CH3:6][C:7]1[CH:8]=[C:9]([C:15]#[N:16])[CH:10]=[N:11][C:12]=1[S:13][CH3:14]>CO>[CH3:6][C:7]1[CH:8]=[C:9]([C:15]([NH2:16])=[O:2])[CH:10]=[N:11][C:12]=1[S:13][CH3:14]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 3826051MethoxideHCID 232882705-Methyl-6-(methylthio)nicotinonitrile

Product 1

HCID 232882605-Methyl-6-methylthio-3-pyridinecarboxamideYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred s odiu m methoxide solution (25 wt % in methanol; 10.53 g, 48.7 mmol) diluted in dry methanol (100 mL) at room temperature under a nitrogen atmosphere was added hydroxylamine hydrochloride (3.38 g, 48.7 mmol) and 5-methyl-6-methylthio-3-pyridinecarbonitrile (2.00 g, 12.2 mmol). The white suspension was stirred at room temperature for 7 days, when it was evaporated in vacuo. The crude white solid was chromatographed on silica gel (25% EtOAc/pentane) yielding the desired product (1.66 g, 75%) as a white fluffy powder.

Workup

  1. customwhen it was evaporated in vacuo
  2. customThe crude white solid was chromatographed on silica gel (25% EtOAc/pentane)

Sources & evidence

ORD record
ord-c111a6ea682044a3ac954bf0c3df281f
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

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