Aluminum → Ethyl 2-amino-2-cyanoacetate

HRID 566432Notes

Reaction equation

HRID 566432 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 mL), 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-78dd2a7ce336441488967dd7b6c23ac8
Source dataset
uspto-grants-2001_01
Patent number
US06174906B1

Reaction notes

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