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Hantzsch synthesis in aqueous solution at low pH range. Pt. I.

Author(s)
A. Ehsan Pakistan Council of Scientific and Industrial Research (PCSIR), Lahore, West-Pakistan
Abstract
The synthesis of Hantzsch ester 1,4-dihydrocol-lidine-3, 5-carboxylate (Ib) in buffered solutions at a pH of 3-10 has been studied. The ester is obtained in good yield (1-53%) at pH 3.25 to 5.0 in 1.0N acetic acid medium. This is in contrast with the observation of Haley and Maitland (1. Chem. Soc., 1951 , 3170). The yellow impurity rioted by them has been found to contain a pyridine derivative of Ib and another basic yellow compound. t3 -Aminocrotonic ester and ethylidene ethyl acetoacetate are the only intermediates during the formation of Ib. The 1,5-diketone on treatment with ammonia gives a compound C H NO ,and not Ib (as reported earlier by Knoevenagel and Klages.Annalen, 1894, 281:105).
Publication Details
Page(s) 5-8
DOI DOI not available
Published Journal: Pakistan Journal of Scientific and Industrial Research, Volume: 11, Issue: 1, Year: 1968

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