Hydroxyamine hydrochloride → HCID 85700068, compound

HRID 2301946Notes

Reaction equation

HRID 2301946 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[OH:21][NH2:22].C([O-])(=O)C.[Na+].C(OCC)(=O)C.CCCCCC>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[N:22][OH:21])[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21226206Ethyl acetate hexaneHCID 22596140HCID 22596140, compound

Product 1

HCID 85700068HCID 85700068, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 3′,4′-dimethoxy-2-propylvalerophenone (2.64 grams, 10 mmol) in a mixture of ethanol (45 milliliters) and water (10 milliliters) was added hydroxyamine hydrochloride (1.11 grams, 16 mmol) and sodium acetate (1.64 grams, 20 mmol) in water (10 milliliters). The solution was refluxed for 1 week. Reaction progress was monitored by TLC (30%, ethyl acetate/hexane, UV) and had reached an equilibrium after 1 week. The reaction was allowed to cool to ambient temperature and the ethanol was removed in vacuo to afford an oil/aqueous mixture which was extracted with methylene chloride, dried over magnesium sulfate and concentrated in vacuo to afford 2.93 grams of crude product as a yellow oil. The crude product was purified by flash chromatography (silica gel, 30%, ethyl acetate/hexane) to afford 1.28 grams (46%) of product as a yellow oil. 1H NMR (CDCl3) δ7.10-6.75(m, 3H), 3.78-3.96(m, 6H), 3.49-3.31(m, 0.5H), 2.65-2.50 (m, 0.5H), 1.91-1.19(m, 8H), 1.01-0.81(m, 6H). 13C NMR (CDCl3) δ162.5, 161.5, 149.5, 149.0, 148.6, 129.4, 125.9, 120.2, 111.2, 110.6, 110.5, 55.9, 55.8, 45.1, 38.9, 34.8, 21.3, 20.5, 14.2.

Workup

  1. temperatureThe solution was refluxed for 1 week
  2. customReaction progress
  3. customafter 1 week
  4. customthe ethanol was removed in vacuo
  5. customto afford an oil/aqueous mixture which
  6. extractionwas extracted with methylene chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford 2.93 grams of crude product as a yellow oil
  10. customThe crude product was purified by flash chromatography (silica gel, 30%, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4148371fe59a4075847deec8c4d72e6c
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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