O-Methylhydroxylamine → HCID 86586324, compound

HRID 585698Notes

Reaction equation

HRID 585698 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1.Cl.[O:17]([NH2:19])C.[C:20]([O-])(=O)C.[Na+].O(N)C>C(O)C>[CH3:20][O:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][CH2:12][C:11](=[N:19][OH:17])[CH2:10]1

Participants

6

Reactant 4

HCID 4113O-MethylhydroxylamineHCID 517045Sodium Acetate2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 12788196(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanone

Product 1

HCID 86586324HCID 86586324, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-3-(2,4-Dihydroxyphenyl)cyclohexanone (22 mg), methoxylamine hydrochloride (18 mg) and sodium acetate (18 mg) were heated under reflux in ethanol. After 6 hr, further methoxylamine (36 mg) and sodium acetate (36 mg) were added and the mixture heated under reflux for a further 1 hr. The reaction mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous layer was extracted with ethyl acetate (2×20 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as a mixture of isomers (18 mg, 72%). δH (CDCl3) 1.5-2.2 (6H, overlapping m), 2.42 (0.5H, bd), 2.69 (0.5H, bd), 2.92 (0.5H, m), 3.06 (0.5H, m), 3.24-3.38 (1H, m), 3.81 (1.5H, s), 3.88 (1.5H, s), 5.42 (0.5H, bs), 5.47 (0.5H, bs), 6.28-6.42 (2H, overlapping m), 6.86 (0.5H, bs), 6.98 (1H, m), 7.06 (0.5H, bs); m/z (ES−) 469 (2M−1)−.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for a further 1 hr
  3. customThe reaction mixture was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate (20 ml) and water (20 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×20 ml)
  6. dry with materialthe combined organic extracts were dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)

Sources & evidence

ORD record
ord-4c97e8eeef22465189c7160757fa10f5
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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