Hydroxyamine hydrochloride → HCID 22344566, compound

HRID 584356Notes

Reaction equation

HRID 584356 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=1.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>C(O)C>[OH:16]/[N:15]=[C:7](\[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)/[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 12487705Ethyl oxo(pyridin-3-yl)acetate

Product 1

HCID 22344566HCID 22344566, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-pyridylglyoxylate (6.00 g), hydroxylamine hydrochloride (2.79 g), sodium acetate (4.13 g) and ethanol (80 ml) was heated to reflux for 15 hours. The reaction mixture was concentrated, water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate to obtain ethyl E-2-hydroxyimino-2-(3-pyridyl)-acetate (3.30 g, yield 51%) as colorless crystals. m.p. 172-173° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe remaining crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f69c1d722b02406c8c1fa2857ddf787f
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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