2103-47-1Relevant academic research and scientific papers
Amidines. Part 20. Rate of Reaction of N,N-Dialkylformamide Acetals with Substituted Anilines
Osek, Jerzy,Oszczapowicz, Janusz,Drzewinski, Witold
, p. 1961 - 1964 (2007/10/02)
Rate of reaction of seven N,N-dialkylformamide acetals R2N-CH(OR2)2 with a series of anilines substituted on the phenyl ring have been measured in benzene, methanol, chloroform, and tetrahydrofuran by use of a g.l.c. method.In each case studied reaction is irreversible and obeys a second-order kinetic equation.Reaction rates correlate with Hammett ? constants for substituents on the phenyl ring of the aniline molecule.On the basis of the kinetic data, the mechanism of reaction is discussed.
A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 5. The Synthesis of 2-Chloroquinoline-3-carbaldehydes
Meth-Cohn, Otto,Narine, Bramha,Tarnowski, Brian
, p. 1520 - 1530 (2007/10/02)
Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution.The reaction is shown to involve successive conversion of the acetanilide into an imidoyl chloride and then an N-(α-chlorovinyl)aniline.The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde.The diformylated intermediates may be isolated in several cases and separately cyclised with polyphosphoric acid.
