Acetic Acid → Ethyl 2-cyano-2-(hydroxyimino)acetate

HRID 1194068Notes

Reaction equation

HRID 1194068 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[N:9]([O-])=[O:10].[Na+].C(O)(=O)C>O>[OH:10][N:9]=[C:5]([C:6]#[N:7])[C:4]([O:3][CH2:1][CH3:2])=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethylcyanoacetate (11.3 g, 100 mmol) is added to a solution of sodium nitrite (8.3 g, 120 mmol) in distilled water (50 ml) and acetic acid (8.0 ml=8.4 g, 140 mmol) is added to the stirred mixture. The ester disappears and soon yellow crystals of the sodium derivative start to separate. Next day the crystals are collected and then dissolved in 2N HCl (50 ml). The product is extracted with ether (four times, 50 ml each time) and the extracts dried over anhydrous Na2SO4. Removal of the solvent by evaporation in vacuo leaves a crystalline residue, ethyl 2-hydroxyimino-2-cyanoacetate, melting at 133° C. (12.4 g, 87%).

Workup

  1. additionis added to the stirred mixture
  2. customsoon yellow crystals of the sodium derivative start to separate
  3. customNext day the crystals are collected
  4. dissolutiondissolved in 2N HCl (50 ml)
  5. extractionThe product is extracted with ether (four times, 50 ml each time)
  6. dry with materialthe extracts dried over anhydrous Na2SO4
  7. customRemoval of the solvent
  8. customby evaporation in vacuo

Sources & evidence

ORD record
ord-45c5f9a4bd6c4bb087b3cee33efb4c00
Source dataset
uspto-grants-1989_03
Patent number
US04812532

Reaction notes

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