Hydroxylamine → N-(3-phenylcyclobutylidene)hydroxylamine

HRID 510764Notes

Reaction equation

HRID 510764 reaction equation
[C:1]1([CH:7]2[CH2:10][C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][OH:13].O>C(O)C.CCOC(C)=O>[C:1]1([CH:7]2[CH2:10][C:9](=[N:12][OH:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 1429633-Phenylcyclobutanone

Product 1

HCID 57357177N-(3-phenylcyclobutylidene)hydroxylamineYield 76.49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-phenylcyclobutanone (0.198 g, 1.354 mmol) in 95% ethanol (7 ml) was added 50% hydroxylamine in water (0.8300 ml, 13.54 mmol), and the reaction was stirred for 16 hours at ambient temperature. The reaction was diluted with EtOAc and washed with water and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to yield 167 mg of the title compound (76.49% yield).

Workup

  1. washwashed with water and saturated sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a7e3092f1134624ab85054f55661866
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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