Methanol → N-(3-phenylcyclobutylidene)hydroxylamine

HRID 2404385Notes

Reaction equation

HRID 2404385 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.CO.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:21][OH:22]>CCOC(C)=O.O>[C:1]1([CH:7]2[CH2:10][C:9](=[N:21][OH:22])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 1429633-PhenylcyclobutanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 57357177N-(3-phenylcyclobutylidene)hydroxylamineYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A yellow slurry of 3-phenylcyclobutanone (1.09 g, 7.44 mmol), MeOH (33.8 mL), water (3.38 mL), potassium carbonate (2.26 g, 16.4 mmol), and hydroxylamine hydrochloride (1.14 g, 16.4 mmol) was heated at 50° C. for 14 hours. The mixture was diluted with EtOAc (50 mL), washed with water (10 mL) and brine (10 mL), dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (0-50% EtOAc/hexanes, gradient elution) to provide the title compound (947 mg, 5.87 mmol, 79% yield). MS (DCI) M/Z 162 [M+H]+.

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (0-50% EtOAc/hexanes, gradient elution)

Sources & evidence

ORD record
ord-426f31ec71d54852b514e4c0972e961c
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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