Hydroxylamine → HCID 136359924, compound

HRID 1631025Notes

Reaction equation

HRID 1631025 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7].[NH2:11][OH:12]>C(O)C>[OH:12][N:11]=[C:6]([NH2:7])[C:5]1[CH:8]=[CH:9][N:10]=[C:3]([CH2:2][OH:1])[CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 132925992-(Hydroxymethyl)pyridine-4-carbonitrile

Product 1

HCID 136359924HCID 136359924, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(hydroxymethyl)isonicotinonitrile (ChemPacific, 0.496 g; 3.7 mmol) and 50% aqueous hydroxylamine (1.2 mL) in ethanol (4.8 mL) was heated at 75° C. for 18 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was poured through a hydrophobic frit and evaporated in vacuo to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.02 (1 H, s), 8.50 (1 H, d, J=5.2 Hz), 7.80 (1 H, s), 7.52 (1 H, dd, J=5.2, 1.7 Hz), 5.99 (2 H, br s), 5.45 (1 H, t, J=5.8 Hz), 4.60 (2 H, d, J=5.8 Hz).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. additionThe organic phase was poured through a hydrophobic frit
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-91b997c12ba449b69dbb72da1fcaab2b
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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