A Convenient One Pot Procedure for N-Methylation of Aromatic Amines Using Trimethyl Orthoformate

REFERENCES AND NOTES

• McGregor , A.L. , Dawson , D. , Owens , J. , Kodama , K. , McCulloch , J. , Magar , S. , Perlman , M. , Zhang , L. and Knapp , A.G. 1995 . Imaging NMDA receptor activation in vivo with [125I] CNS 1261A . Soc. Neurosci. Abstract , : 250.16
   Google Scholar
• March , J. 1992 . Advanced Organic Chemistry , 1212 – 1213 . New York : John Wiley & Sons .
   Google Scholar
• Ladenburg , A. 1877 . Ber. , 10 : 1123
   Google Scholar
• Roberts , R.M. and Vogt , P.J. 1956 . J. Am. Chem. Soc. , 78 : 4778
   Web of Science ®Google Scholar
• Roberts , R.M. and Vogt , P.J. 1963 . Org. Synth. Coll. Vol. , IV : 420
   Google Scholar
• Ramarao , K.U. , Ramkumar , C.A. , Anant , N.A. and Ramanuja , A.N. 1991 . Synth. Commun. , 21 : 1129 and the references cited therein
   Google Scholar
• Briggs , E.M. , Brown , G.W. , Jiricny , J. and Meidine , M.F. 1980 . Synthesis , : 295
   Google Scholar
• Sekiya , M. and Ito , K. 1966 . Chem. Pharm. Bull. , 14 : 1007
   Google Scholar
• Halasz , A. 1969 . Chem. Ind. , : 1701
   Google Scholar
• Strazzolini , P. , Giumanini , A.G. and Cauci , S. 1990 . Tetrahedron , 46 : 1081
   Web of Science ®Google Scholar
• Icko , R.N. , Wisegarver , B.B. and Allen , G.A. 1955 . Org. Synth. Coll. Vol. , III : 723
   Google Scholar
• Borch , R.F. , Bernstein , M.D. and Durst , H.D. 1971 . J. Am. Chem. Soc. , 93 : 2897
   Web of Science ®Google Scholar
• For reviews refer a) Gribble G.W. Nutaitis C.F. Org. Prep. Proced. Int. 1985 17 317
   Web of Science ®Google Scholar
• Hutchins , R.O. and Natale , N. 1979 . Org. Prep. Proced. Int. , 11 : 201
   Web of Science ®Google Scholar
• Bhattacharya , S. 1995 . Synth. Commun. , 25 : 2061 and the references cited therein
   Google Scholar
• Pine , S.H. and Sanchez , B.L. 1971 . J. Org. Chem. , 36 : 829
   Web of Science ®Google Scholar
• Seikya , M. and Ito , K. 1967 . Chem. Pharm. Bull. , 15 : 1339
   PubMedGoogle Scholar
• Kadin , S.B. 1973 . J. Org. Chem. , 38 : 1348
   Google Scholar
• Huebner , C.F. , Donoghue , E.M. , Plummer , A.J. and Furnea , P.A. 1966 . J. Med. Chem. , 9 : 830
   PubMedGoogle Scholar
• Friedman , O.M. , Parameswaran , K. N. and Burstein , S. 1963 . J. Med. Chem. , 6 : 227
   PubMedGoogle Scholar
• Weiss , B. 1965 . J. Org. Chem. , 30 : 2483
   Google Scholar
• Crochet , R.A. Jr. and Blanton , C.D. Jr. 1974 . Synthesis , : 55
   Google Scholar
• Gribble , G.W. , Lord , P.D. , Skotnicki , J. , Dietz , S.E. , Eaton , J.T. and Johnson , J. L. 1974 . J. Am. Chem. Soc. , 96 : 7812
   Web of Science ®Google Scholar
• Marchini , P. , Liso , G. , Reho , A. , Liberatore , F. and Moracci , F.M. 1975 . J. Org. Chem. , 40 : 3453
   Web of Science ®Google Scholar
• Barton , D.H.R. , Ozbalik , N. and Ramesh , M. 1988 . Tetrahedron Lett. , 29 : 857
   Web of Science ®Google Scholar
• Bulychev , Yu. N. , Preobrazhenskaya , M.N. , Chernyshev , A.I. and Esipov , S.E. 1988 . Khim. Geterotsikl. Soedin. , 7 : 756 (Chem. Abstr., 111, 135157s, 1989) and the references cited therein
   Google Scholar
• van Meurs , N. 1968 . Recl. Trav. Chim. Pays-Bas. , 87 : 145
   Google Scholar
• The final guanidine derivatives derived from the N-methylaniline derivatives (7a & 7b) gave satisfactory microanalyses, 1H-NMR, MS data and HPLC purity.
   Google Scholar
• Baeyer , A. 1905 . Chem. Ber. , 38 : 2762
   Google Scholar
• Galliani , G. and Rindone , B. 1976 . J. Chem. Commun. , : 782
   Google Scholar
• Melloni , P. , Metelli , R. , Vecchietti , V. , Logemann , W. , Castellino , S. , Monti , G. and De Carneri , I. 1974 . Eur. J. Med. Chem. - Chimica Therapeutica , 9 : 26
   Web of Science ®Google Scholar
• Julia , M. and Lenzi , J. 1962 . Bull. Soc. Chim. France , : 1051
   Google Scholar
• Jlocum , W. and Jennings , C.A. 1976 . J. Org. Chem. , 41 : 3653
   Google Scholar
• Teutscher , H. 1918 . Liebigs. Ann. Chem. , 416 : 189
   Google Scholar
• Coppola , G.M. and Schuster , H.F. 1989 . J. Heterocycl. Chem. , 26 : 957
   Web of Science ®Google Scholar
• HPLC purity estimation was not carried out.
   Google Scholar
• Meldola , R. and Salmon , E.H.R. 1888 . J. Chem. Soc. , 53 : 775
   Google Scholar
• Tingle , J.B. and Blanck , F.C. 1908 . J. Am. Chem. Soc. , 30 : 1405
   Google Scholar