Aluminum → Ethyl 2-amino-2-cyanoacetate

HRID 378230Notes

Reaction equation

HRID 378230 reaction equation
[Al].O[N:3]=[C:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]>O.C(OCC)C.[Hg](Cl)Cl>[NH2:3][CH:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 2

HCID 5359268AluminumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 288716Ethyl 2-amino-2-cyanoacetateYield 74.7%

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To aluminum foil (25 g) was added a solution of mercury(II) chloride (10 g, 0.37 mol) in water (1 L). The mixture was swirled for 5 min, and then the turbid solution was decanted off. The resulting aluminum amalgam was washed successively with water, methanol and diethyl ether. To amalgam suspended in diethyl ether (500 mL) at 0° C., was added a solution of ethyl 2-hydroxyimino-2-cyanoacetate (100 g, 0.70 mol) in diethyl ether (300 mL), followed by water (50 mnL), maintaining a gentle reflux. After 1 h of stirring, the mixture was filtered and the filtrate was washed with water, brine and dried (Na2SO4). Removal of the solvent gave the title compound as a white solid (67 g, 74%). 1H NMR (250 MHz, CD3OD)δ 4.45 (m, 2H), 2.49 (s, 1H), 1.38 (m, 3H).

Workup

  1. customthe turbid solution was decanted off
  2. washThe resulting aluminum amalgam was washed successively with water, methanol and diethyl ether
  3. customsuspended in diethyl ether (500 mL) at 0° C.
  4. temperaturemaintaining a gentle reflux
  5. filtrationthe mixture was filtered
  6. washthe filtrate was washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-299930b2f7bd4084a8e64080df4e56db
Source dataset
uspto-grants-2000_02
Patent number
US06030970

Reaction notes

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