Pyridine → HCID 86663514, compound

HRID 2406556Notes

Reaction equation

HRID 2406556 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=1.N1C=CC=CC=1>C(O)C>[CH3:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[N:2][OH:3])[CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 66821931HCID 66821931, compound

Product 1

HCID 86663514HCID 86663514, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (2.7 g, 39.4 mmol) was added to a stirred solution of 1-(4-(methoxymethoxy)-phenyl)butan-1-one (4.1 g, 19.7 mmol) and pyridine (94.67 g, 59.1 mmol) in ethanol (30 mL), and the mixture heated to reflux for 1.5 hours then allowed to cool. Most of the ethanol was removed by concentration under reduced pressure, and the residue was partitioned between water and dichloromethane. The layers were separated and the aq phase extracted 2× with dichloromethane. The combined extracts were washed twice with water, then with saturated brine and dried over magnesium sulfate. The solvent was removed in vacuo, leaving 5.1 g of slightly cloudy, colorless syrup, which was flash chromatographed on a column (50×70 mm) of silica gel eluting with Hxa/EtOAc/acetone 8:1:1 to afford 3.4 g (77%) of snow-white crystalline solid; mp 74-76° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. customMost of the ethanol was removed by concentration under reduced pressure
  5. customthe residue was partitioned between water and dichloromethane
  6. customThe layers were separated
  7. extractionthe aq phase extracted 2× with dichloromethane
  8. washThe combined extracts were washed twice with water
  9. dry with materialwith saturated brine and dried over magnesium sulfate
  10. customThe solvent was removed in vacuo
  11. customleaving 5.1 g of slightly cloudy, colorless syrup, which
  12. customchromatographed on a column (50×70 mm) of silica gel eluting with Hxa/EtOAc/acetone 8:1:1

Sources & evidence

ORD record
ord-10fd897902e148989c1efd9aee13c1a8
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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