Water → 3-(Cyanomethyl)pyridin-1-ium-1-olate

HRID 1678132Notes

Reaction equation

HRID 1678132 reaction equation
C(OO)(=[O:3])C.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C:13]#[N:14])[CH:7]=1.O>C(O)(=O)C>[CH:10]1[CH:11]=[N+:6]([O-:3])[CH:7]=[C:8]([CH2:12][C:13]#[N:14])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6585Peracetic AcidHCID 809233-Pyridineacetonitrile

Product 1

HCID 2431673-(Cyanomethyl)pyridin-1-ium-1-olate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

The title compound is prepared in accordance with the procedures as outlined in S. Okuda et al., J. Am. Chem. Soc., 81, 740, (1959). Peracetic acid (38%, 40 mL, 0.2 mol) is added to a stirred solution of 3-pyridylacetonitrile (15.0 g, 127 mmol) in acetic acid (75 mL) and the reaction is heated at 95° C. for 24 hr, then stirred at room temperature for 24 hr. Water is added and the solvents are removed. More water (100 mL) is added and again removed. This process is repeated with toluene and with ether to give (1-oxypyridin-3-yl)acetonitrile as a cream solid.

Workup

  1. customThe title compound is prepared in accordance with the procedures
  2. customthe solvents are removed
  3. additionMore water (100 mL) is added
  4. customagain removed

Sources & evidence

ORD record
ord-e5212419bdd5444587ff7e325600fe69
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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