N-Phenylhydroxylamine → HCID 15656242, compound

HRID 1608708Notes

Reaction equation

HRID 1608708 reaction equation
O1CCOCC1.[CH2:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CN(C)P(N(C)C)(N(C)C)=O.[C:26]1([NH:32]O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:26]1([NH:32][CH2:7]/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7518N-PhenylhydroxylamineHCID 81251-OcteneHCID 12679HexamethylphosphoramideHCID 312751,4-Dioxane

Product 1

HCID 15656242HCID 15656242, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture containing dioxane (12 mL), 3 mL of 1-octene, 1 g of 4A Molecular Sieves, and 0.051 g (0.11 mmol) of (2,6-dipicolinato)MoO2 (hexamethyl phosphoramide) is heated at reflux (ca. 100° C.) under a nitrogen atomosphere 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 6-12 hr, the mixture was allowed to cool and the volatiles were removed by evaporation at reduced pressure and the residue chromatographed over silica gel. Elution with pentane afforded phenyl trans-2-octenyl amine (>95% one isomer by NMR, GC/MS) in 20-30% 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 6-12 hr
  4. temperatureto cool
  5. customthe volatiles were removed by evaporation at reduced pressure
  6. customthe residue chromatographed over silica gel
  7. washElution with pentane

Sources & evidence

ORD record
ord-ee03df1979dd45afb93a87f83c100e5c
Source dataset
uspto-grants-1995_03
Patent number
US05395971

Reaction notes

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