Hydroxyamine hydrochloride → 1-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one Oxime

HRID 660566Notes

Reaction equation

HRID 660566 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28])[CH2:12][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][C:14]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C([O-])(=O)C.[Na+]>CCO.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28])[CH2:12][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][C:14]1=[N:31][OH:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 688398621-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 866325751-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one Oxime

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of 1-(3-benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one (600 mg, 1.55 mmol), hydroxylamine hydrochloride (160 mg, 2.32 mmol) and sodium acetate (254 mg, 3.10 mmol) in 6 mL EtOH/H2O (2:1) is refluxed for 2 h. The solution is cooled to RT and extracted with CH2Cl2. The organic layer is washed with water, brined and dried over MgSO4. The solvent is removed under reduced pressure and the residue is purified by flash chromatography with CH2Cl2 to give the title compound as a yellow liquid. (M+1)+=403.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer is washed with water
  3. dry with materialdried over MgSO4
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by flash chromatography with CH2Cl2

Sources & evidence

ORD record
ord-35ca115da7b14791ba187acd463a6026
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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