3-Pyridinemethanol → 1-Amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolate

HRID 1639739Notes

Reaction equation

HRID 1639739 reaction equation
[NH2:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1>C(#N)C>[N+:12]([C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O-:2])([O-:14])=[O:13].[NH2:1][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 87140O-(2,4-dinitrophenyl)hydroxylamine

Product 1

HCID 866419191-Amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolateYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(aminooxy)-2,4-dinitrobenzene (117 g, 0.590 mol) in acetonitrile (1.18 L) was added 3-pyridinemethanol (64.1 g, 0.590 mol) at 40° C., and the mixture was stirred for 24 hr. The solvent was evaporated under reduced pressure, and the residue was washed with dichloromethane (1 L×2) to give the title compound (150 g, yield 83%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was washed with dichloromethane (1 L×2)

Sources & evidence

ORD record
ord-1022f9aff398478f88a661644c6e2e9c
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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