Hydroxylamine → N'-hydroxy-6-(hydroxymethyl)nicotinimidamide

HRID 1631032Notes

Reaction equation

HRID 1631032 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]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 534276876-(Hydroxymethyl)pyridine-3-carbonitrile

Product 1

HCID 86660279N'-hydroxy-6-(hydroxymethyl)nicotinimidamideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. customevaporated in vacuo
  4. washThe resultant solid was washed with MeCN
  5. customdried

Sources & evidence

ORD record
ord-8686ebc40ad64d338f3045ee471a6bdd
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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