Water → Ethyl 2-amino-2-(hydroxyimino)acetate

HRID 966420Notes

Reaction equation

HRID 966420 reaction equation
[OH2:1].[C:2]([C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:3].Cl.[NH2:10]O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:3][C:2](=[N:10][OH:1])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 69336Ethyl cyanoformateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Water (600 ml) is added dropwise over a period of two hours to a vigorously stirred, room temperature mixture of ethyl cyanoformate (99 g, 1 mol), hydroxylamine hydrochloride (105 g, 1.5 mol ) and sodium carbonate (82 g, 0.77 mol ) in ethanol (1 L.) The resulting solution is stirred until the starting material has been consumed. When the reaction is complete, most of the solvent is removed in vacuo and the resulting residue is extracted with methylene chloride (3×200 ml.) The combined organic extracts are washed with brine (250 ml), dried (Na2SO4), filtered and concentrated to afford 120.1 g (91%) of compound 2a as a white solid. Further purification can be achieved by crystallization from chloroform and hexanes. 1H NMR (CDCl3): δ9.15 (br s, OH), 5.12 (br s, 2H), 4.32 (q, 2H), 1.42 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3): δ161.4, 144.4, 62.8, 14.3.

Workup

  1. stirringis stirred until the starting material
  2. customhas been consumed
  3. customis removed in vacuo
  4. extractionthe resulting residue is extracted with methylene chloride (3×200 ml.) The combined organic extracts
  5. washare washed with brine (250 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-08d04c05f4074dbc8ff640fdd1b25567
Source dataset
uspto-grants-2005_10
Patent number
US06951946B2

Reaction notes

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