Butyl nitrite → alpha-Oximino-3-pyridylacetonitrile

HRID 2286260Notes

Reaction equation

HRID 2286260 reaction equation
[O-]CC.[Na+].[Na].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C:13]#[N:14])[CH:7]=1.[N:15](OCCCC)=[O:16]>C(O)C>[OH:16][N:15]=[C:12]([C:8]1[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=1)[C:13]#[N:14]

Participants

6

Reactant 4

HCID 10996Butyl nitriteHCID 809233-PyridineacetonitrileHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 72747148alpha-Oximino-3-pyridylacetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of sodium ethoxide in anhydrous ethanol, prepared from 5 g of sodium and 50 ml of anhydrous ethanol, 24 g of 3-pyridineacetonitrile was added, followed by dropwise addition of 21 g freshly distilled n-butyl nitrite. The reaction mixture was stirred for another hour and the precipitated sodium salt of the oxime was filtered and washed with ether. The free oxime was obtained by acidification of an aqueous solution of the salt and recrystallization from water, yielding 17 g (58%) of the title compound. M.p. 234°-238° C. under decomposition. Usually, the salt was directly used in succeeding reactions.

Workup

  1. additionwas added
  2. filtrationthe precipitated sodium salt of the oxime was filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-2fb5eb55bdb8440ead2e099dcd6bd0b4
Source dataset
uspto-grants-1982_04
Patent number
US04327213

Reaction notes

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