Sodium Dithionite → Ethyl 2-amino-2-cyanoacetate

HRID 2244424Notes

Reaction equation

HRID 2244424 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[C:5]([C:8]#[N:9])=[N:6]O)[CH3:2].C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([NH2:6])[C:8]#[N:9])[CH3:2]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 288716Ethyl 2-amino-2-cyanoacetateYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyano-hydroxyimino-acetic acid ethyl ester (30.00 g, 211.10 mmol) was added portionwise to a solution of water (766.00 ml) and saturated sodium bicarbonate (192.00 ml). Sodium dithionite (73.50 g, 422.00 mmol) was then added during 5 min. The mixture was stirred at room temperature for 2 hours, then extracted four times with dichloromethane. The combined organic extracts were dried with Na2SO4 and evaporated to afford aminocyanacetic acid ethyl ester as a light yellow oil (11.80 g, 44%).

Workup

  1. extractionextracted four times with dichloromethane
  2. dry with materialThe combined organic extracts were dried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-0e75a6be8bbc49a1be7ee9947f9de99a
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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