Ethylene → Aniline

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

Reactant 3

HCID 6325Ethylene

HCID 70602-Methylquinoline

HCID 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.