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

HRID 495983

Reaction equation

HRID 495983 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[NH2:12][OH:13]>C(O)C.O>[C:1]1(=[N:12][OH:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 107241-Tetralone

Product 1

HCID 76876N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5 mL (37.5 mmole) 1-tetralone in 25 mL ethanol was added 2.7 mL (40 mmole) of 50% hydroxylamine in water. The reaction mixture was heated under reflux for 2 hrs, then stirred at room temperature for 16 hrs. The solution was concentrated under reduced pressure. The residue was recrystallized from toluene/hexane to give 1-tetralone oxime (3,4-dihydro-2H-naphthalen-1-one oxime), 3.86 g, m.p. 101-102°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe solution was concentrated under reduced pressure
  4. customThe residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-2acf8498a3144385b07360a027384d7e
Source dataset
uspto-grants-2005_09
Patent number
US06943169B2

Linked notes

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