Nitrobenzene → Azoxybenzene

HRID 1648604Notes

Reaction equation

HRID 1648604 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=O.O.O.[OH-].C[N+:14]([CH3:17])(C)C>C(#N)C1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[N:14][C:17]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1)[O-:3]

Participants

4

Reactant 2

HCID 7416NitrobenzeneHCID 22116808Tetramethylammonium hydroxide dihydrate

Product 1

HCID 10316AzoxybenzeneYield 45%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing 10 g of nitrobenzene, 1.27 g of tetramethylammonium hydroxide dihydrate and 1 g of benzonitrile was stirred at 60° C. with nitrogen bubbled into the solution via a syringe needle for 1 hour. Analysis of a sample of the reaction product by HPLC revealed N-(4-nitrophenyl)-benzamide was produced in 45% yield and azoxybenzene was generated in 22% yield based on tetramethylammonium hydroxide.

Workup

  1. custombubbled into the solution via a syringe needle for 1 hour

Sources & evidence

ORD record
ord-8c37f1219c634a3799c46187d1f88a83
Source dataset
uspto-grants-1995_07
Patent number
US05436371

Reaction notes

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