Hydroxyamine hydrochloride → HCID 86674675, compound

HRID 625925Notes

Reaction equation

HRID 625925 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][OH:23]>C(O)C>[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[CH2:11][CH2:10][C:9]1=[N:22][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 214101101-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one

Product 1

HCID 86674675HCID 86674675, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4.47 mmol of 1-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one in 15 ml ethanol were added 5.59 mmol hydroxylamine hydrochloride (dissolved in 3 ml water). The solution was stirred at 65° C. for 1.5 h. The mixture was cooled to RT and concentrated. The residue was dissolved in methyl tert-butylether and washed with water (2×), dried over MgSO4 and filtered. Evaporation of the solvent gave 1.29 g of 1-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one oxime (mixture of E- and Z-isomer, 100%).

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methyl tert-butylether
  4. washwashed with water (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-eb89f3750d554ba094764bdac84c41ab
Source dataset
uspto-grants-2016_04
Patent number
US09309200B2

Reaction notes

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