Hydroalkylation of Aniline with Pd-Al2O3 and NaCl-AlCl3

The hydroalkylation of aniline in a palladium-fused salt system was examined under hydrogen pressure. By using 0.5% Pd-Al2O3 and fused salt (NaCl-AlCl3), N-cyclohexylaniline (4) was formed as the main product at temperatures below 300°C ; at higher temperatures, the cyclohexyl group rearranged to fo...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 30; no. 3; pp. 777 - 781
Main Authors KAMIYAMA, TSUTOMU, ENOMOTO, SABURO, INOUE, MASAMI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 01.01.1982
Japan Science and Technology Agency
Subjects
dicyclohexylamine
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Summary:The hydroalkylation of aniline in a palladium-fused salt system was examined under hydrogen pressure. By using 0.5% Pd-Al2O3 and fused salt (NaCl-AlCl3), N-cyclohexylaniline (4) was formed as the main product at temperatures below 300°C ; at higher temperatures, the cyclohexyl group rearranged to form nuclear alkylated products, o-and p-cyclohexylaniline, (5) and (6). The yield of 4 was 27.7% at 280°C ; those of 5 and 6 were 5.4 and 7.3%, respectively, at 400°C. The reaction mechanism for the hydroalkylation of aniline with this catalytic system is discussed.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.30.777