Pyridine → HCID 74315225, compound

HRID 2406566Notes

Reaction equation

HRID 2406566 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH3:17])=[CH:11][CH:10]=1.N1C=CC=CC=1>C(O)C>[CH3:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[N:2][OH:3])[CH2:16][CH3:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 20109578HCID 20109578, compound

Product 1

HCID 74315225HCID 74315225, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (2.27 g, 32.7 mmol) was added to a stirred solution of 1-(4-(2-methoxyethoxy)phenyl)propan-1-one (3.4 g, 16.3 mmol) and pyridine (3.87 g, 49.0 mmol) in ethanol (25 mL) and the mixture heated at reflux for 4 hours then allowed to cool. Most of the ethanol was removed by concentration, and the residue was partitioned between water and dichloromethane. The layers were separated and the aqueous phase extracted 2× with dichloromethane. The combined extracts were washed twice with water, then with sat brine and dried over magnesium sulfate. The solvent was removed by concentration, and then the residue was dissolved in toluene and again concentrated; this process was repeated once more, and the residue was dried under in vacuo to afford 3.52 g of the product as a cream-colored crystalline solid; mp 74-80° C.; mass spec ES+m/z=224 (m+1).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. customMost of the ethanol was removed by concentration
  5. customthe residue was partitioned between water and dichloromethane
  6. customThe layers were separated
  7. extractionthe aqueous phase extracted 2× with dichloromethane
  8. washThe combined extracts were washed twice with water
  9. dry with materialwith sat brine and dried over magnesium sulfate
  10. customThe solvent was removed by concentration
  11. dissolutionthe residue was dissolved in toluene
  12. concentrationagain concentrated
  13. customthe residue was dried under in vacuo

Sources & evidence

ORD record
ord-05450010f05846feaa9f92e6f59ce178
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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