Ethyl 2-cyano-2-(hydroxyimino)acetate → Ethyl 2-amino-2-cyanoacetate

HRID 879135Notes

Reaction equation

HRID 879135 reaction equation
[C:1]([C:3](=[N:9]O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>C(O)C.O=[Pt]=O>[NH2:9][CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

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

Product 1

HCID 288716Ethyl 2-amino-2-cyanoacetateYield 89%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-cyano-2-(hydroxyimino)acetate (1 eq) in ethanol (1.4 M) was added PtO2 (0.05 eq) and the solution was put under an H2 atmosphere (4 bar) in a steel bomb and was stirred overnight. The reaction was filtered through a pad of celite, rinsing with CH2Cl2 and upon removal of volatiles in vacuo ethyl 2-amino-2-cyanoacetate was obtained in 89% yield. LC/MS (m/z): 129.0 (MH+), Rt: 0.25 min.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washrinsing with CH2Cl2 and upon removal of volatiles in vacuo ethyl 2-amino-2-cyanoacetate
  3. customwas obtained in 89% yield

Sources & evidence

ORD record
ord-c412a04546d846328887eb2abcf280ab
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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