Potassium iodide catalysed monoalkylation of anilines under microwave irradiation

Tetrahedron Letters

Volumn 45, Issue 48, 2004, Pages 8797-8800

  Romera, Juan L ^a   Cid, José M ^a   Trabanco, Andrés A ^a  

^a Jarama S/n 45007 Toledo Spain   (Spain)

Author keywords

Aniline; Microwave assisted synthesis; N Alkylation

Indexed keywords

ANILINE DERIVATIVE; POTASSIUM IODIDE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 7444260195     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.002     Document Type: Article

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23. The excess of aniline can be easily recovered during the HPLC purification step
24. 3 and KI the product 3a was obtained in 7% yield after microwave irradiation at 110°C for 10 min
25. 13C NMR and high resolution mass spectrometry
26. When the reaction mixture was heated at 110°C (oil bath temperature) for 10 min into a sealed tube the monoalkylation product 3a was obtained in 60% yield
27. When the alkylation reaction with 2b, h or 2k was performed in an open vessel with a catalytic amount of KI (0.1 equiv) in refluxing acetonitrile (traditional heating) for 1 h, the corresponding products 3b, h or 3k were obtained in 57%, 52% and 80%, respectively
28. 2O 221.1654, found 221.1658
29. Typical pressures for reactions carried out at 110°C, 170°C and 190°C are, respectively, 1.1, 6.5 and 12 bar