3-Pyridinecarboxaldehyde → HCID 3055794, compound

HRID 2232091Notes

Reaction equation

HRID 2232091 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.Cl.[CH2:10]([O:12][NH2:13])[CH3:11]>CO>[CH2:10]([O:12][N:13]=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:11]

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 76850O-ethylhydroxylamine hydrochloride

Product 1

HCID 3055794HCID 3055794, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Pyridinecarboxaldehyde (10.7 100 mmol) and ethoxyamine, hydrochloride (10 g, 102.5 mmol) were dissolved in CH3OH (100 ml) and heated at reflux for three hours. The solvent was removed under vacuum and 10% aqueous Na2CO3 solution was added to the residue until the solution remained basic. The aqueous solution was extracted with EtOAc (3×100 ml), dried over MgSO4, filtered, and the solvent removed under vacuum. 13.2 g of 3-pyridinecarboxaldehyde-O-ethyloxime as a clear liquid was obtained 88% yield.

Workup

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. customThe solvent was removed under vacuum and 10% aqueous Na2CO3 solution
  4. additionwas added to the residue until the solution
  5. extractionThe aqueous solution was extracted with EtOAc (3×100 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-0279842a14c342b8aea8e74ca3963188
Source dataset
uspto-grants-1988_11
Patent number
US04786648

Reaction notes

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