Ethylene → Aniline

HRID 236802

Reaction equation

HRID 236802 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C=C.CC1C=CC2C(=CC=CC=2)N=1>>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6325EthyleneHCID 70602-MethylquinolineHCID 7416Nitrobenzene

Product 2

HCID 6115AnilineYield 7.1%HCID 7416Nitrobenzene

Conditions

Temperature
160 °C

Procedure

Twenty grams of nitrobenzene and 1.1 grams of iodo (4-iodophenyl) bis(triphenylphosphine)-palladium was placed in a 300 ml. stainless steel rocking autoclave. This was sealed and pressurized with ethylene to 600 psi and heated to 160° C. This temperature was maintained for 17 hours. The autoclave was then cooled and vented. After opening the vessel the reaction mixture was analyzed by gas chromatography. This analysis showed that 6.8 grams of 2-methylquinoline (54.0% efficiency) was obtained together with 0.6 grams of aniline (7.1% efficiency) and 7 grams of unreacted nitrobenzene.

Workup

  1. customThis was sealed
  2. temperatureThis temperature was maintained for 17 hours
  3. temperatureThe autoclave was then cooled

Sources & evidence

ORD record
ord-aec30557fa214165851007ec1a03f945
Source dataset
uspto-grants-1979_06
Patent number
US04157445

Linked notes

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