Sodium Dithionite → Ethyl 2-amino-2-cyanoacetate

HRID 374885Notes

Reaction equation

HRID 374885 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([C:11](=[N:17]O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]>O.C(=O)([O-])O.[Na+]>[NH2:17][CH:11]([C:9]#[N:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 288716Ethyl 2-amino-2-cyanoacetateYield 37.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
35 °C

Procedure

119 g of sodium dithionite are added in portions (15 min) at room temperature to 35 g (0.246 mol) of ethyl 2-cyanoglyoxylate-2-oxime in 350 ml of H2O and 280 ml of saturated sodium hydrogen carbonate solution. The mixture is then warmed at 35° C. for 1 hour; it is then saturated with NaCl and extracted 5 times with dichloromethane. After drying with calcium chloride, the organic phase is concentrated. 11.8 g of the title compound are obtained as an oil.

Workup

  1. extractionsaturated with NaCl and extracted 5 times with dichloromethane
  2. dry with materialAfter drying with calcium chloride
  3. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-235fc25abea847fa96cceaa33bd6c79f
Source dataset
uspto-grants-1996_01
Patent number
US05482957

Reaction notes

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