N-Phenylhydroxylamine → N-(Cyclohex-3-en-1-yl)aniline

HRID 1608709Notes

Reaction equation

HRID 1608709 reaction equation
O1CCOCC1.[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1.[C:13]1([NH:19]O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[C:7]1([NH:19][CH:13]2[CH2:18][CH2:17][CH:16]=[CH:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7518N-PhenylhydroxylamineHCID 8079CyclohexeneHCID 312751,4-Dioxane

Product 1

HCID 20087164N-(Cyclohex-3-en-1-yl)anilineYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture containing dioxane (12 mL), 3 mL of cyclohexene, 1 g of 4A Molecular Sieves, and 0.11 mmol of (2,6-dipicolinato)(HMPA)Mo(O)(ONPh) is heated at reflux (ca. 100° C.) under a nitrogen atmosphere while a toluene solution (50 mL) of N-phenyl hydroxylamine (1.26 g, 11.6 mmol) is added dropwise over a 24 hr period. After heating an additional 12-24 hr, the mixture was allowed to cool and the volatiles were removed by evaporation at reduced pressure. Chromatography of the residue over silica gel and elution with pentane afforded phenyl 3-cyclohexenyl amine (>95% one isomer by NMR, GC/MS) in 15-25% yield based on the hydroxylamine. Later fractions contained aniline, azobenzene and azoxybenzene.

Workup

  1. temperatureis heated
  2. additionis added dropwise over a 24 hr period
  3. temperatureAfter heating an additional 12-24 hr
  4. temperatureto cool
  5. customthe volatiles were removed by evaporation at reduced pressure
  6. washChromatography of the residue over silica gel and elution with pentane

Sources & evidence

ORD record
ord-cda4bbfa603c49ada02cc57ecf3f74a3
Source dataset
uspto-grants-1995_03
Patent number
US05395971

Reaction notes

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