Hydroxyamine hydrochloride → 5-n-Butylindan-1-one oxime

HRID 19716Notes

Reaction equation

HRID 19716 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH2:9]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=O)[CH2:17][CH2:16]2)[CH2:10][CH2:11][CH3:12]>C(O)C.O>[CH2:9]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[N:2][OH:3])[CH2:17][CH2:16]2)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 149399645-n-Butylindan-1-one

Product 1

HCID 860040385-n-Butylindan-1-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Hydroxylamine hydrochloride (0.89 g, 12.8 mmol) and sodium acetate (12.8 mmol) are added to a solution of 5-n-butylindan-1-one (1.0 g, 5.31 mmol) in ethanol (30 ml) and water (3 ml). The reaction is heated to reflux for 20 minutes, then water is added and the mixture is extracted with CH2Cl2. The combined organic extracts are washed with brine, dried (MgSO4) and evaporated to afford the title compound. NMR δH 0.86 (t J 7.3 3H), 1.28 (sextet J 7.3 2H), 1.52 (quintet J 7.3 2H), 2.55 (t J 8.0 2H), 2.85-3.0 (m 4H), 7.0 (d J 8.3 1H), 7.05 (s 1H), 7.45 (d J 8.3 2H)

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 20 minutes
  3. extractionthe mixture is extracted with CH2Cl2
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f90580b923b54dcea6cf2698b7828a3e
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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