1-Tetralone → N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine

HRID 910066Notes

Reaction equation

HRID 910066 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]1[CH2:14][C:12](=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1>CO>[C:12]1(=[N:2][OH:3])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:14]1

Participants

4

Reactant 2

HCID 107241-TetraloneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 76876N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamineYield 63.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

Add hydroxylamine hydrochloride (71.0 g, 1.03 mol) to a solution of α-tetralone (100.0 g, 0.68 mol) in 300 mL of methanol and stir the resulting solution at reflux for 2 hours. Cool the mixture to 20-24° C. and concentrate under reduced pressure. Dilute the residue with 1 L of water and extract with dichloromethane. Wash the organic layer with saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate under reduced pressure. Crystallize the residue from isopropanol to provide the desired compound as an off-white solid (70.0 g, 63%).

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrate under reduced pressure
  3. additionDilute the residue with 1 L of water
  4. extractionextract with dichloromethane
  5. washWash the organic layer with saturated aqueous sodium chloride
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customCrystallize the residue from isopropanol

Sources & evidence

ORD record
ord-2886b1a562c343b59f883f558650f464
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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