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

HRID 351573

Reaction equation

HRID 351573 reaction equation
[CH2:1]1[CH2:11][C:9](=O)[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.Cl.[NH2:13][OH:14]>CO>[C:9]1(=[N:13][OH:14])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH2:11]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

To a solution of α-tetralone (100.0 g, 0.68 mol) in 300 mL of methanol was added hydroxylamine hydrochloride (71.0 g, 1.03 mol) and the resulting solution was stirred at reflux for 2 hours. The mixture was allowed to cool to 20-24° C. and was concentrated under reduced pressure. The resulting mixture was diluted with 1 L of water and extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from isopropanol to provide 70.0 g (63%) of the desired compound as an off-white solid.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationwas concentrated under reduced pressure
  3. additionThe resulting mixture was diluted with 1 L of water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-54e1e56f3d4d41a199e6f95cff67b043
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Linked notes

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