Nitrobenzene → Quinoline

HRID 236803Notes

Reaction equation

HRID 236803 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH2:10]=[CH:11][CH3:12]>>[N:1]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 7416NitrobenzeneHCID 8252Propylene

Product 1

HCID 7047Quinoline

Conditions

Temperature
220 °C

Procedure

Twenty grams of nitrobenzene, 1.1 grams of iodo (4-iodophenyl) bis(triphenylphosphine)palladium catalyst and 39 grams of liquified propylene was placed in a 300 ml. stainless steel rocking autoclave and cooled to -78° C. The vessel was sealed and heated to 220° C. This temperature was maintained for 24 hours. The autoclave was then cooled and vented. The reaction mixture removed from the autoclave was analyzed by gas chromatography and found to contain 0.32 grams of quinoline (1.9% efficiency) 5.8 grams of aniline (44.0% efficiency) and 2.8 grams of unreacted nitrobenzene.

Workup

  1. customThe vessel was sealed
  2. temperatureThis temperature was maintained for 24 hours
  3. temperatureThe autoclave was then cooled
  4. customThe reaction mixture removed from the autoclave

Sources & evidence

ORD record
ord-43e7917e452f4ed7be8105469337554a
Source dataset
uspto-grants-1979_06
Patent number
US04157445

Reaction notes

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