Preparation of 3-(pyridinyl)-2-cyclohexen-1-ones

Details Preparation of 3-(pyridinyl)-2-cyclohexen-1-ones Preparation of 3-(pyridinyl)-2-cyclohexen-1-ones

1977-07-29

1978-09-05

Randolph, John D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D21346

Patent

active

041119460

ABSTRACT:
3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)-pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

REFERENCES:
patent: 4026900 (1977-05-01), Gelotte et al.
Marvel et al., J. Org. Chem., vol. 22, pp. 1451 to 1457 (1957).
Mohrle et al., Arch. Pharmaz., vol. 307, pp. 550 to 560 (1974).
Compagnon et al., Bull Soc Chim France 1968, pp. 4132 to 4136.
Ross et al., J. Org. Chem., vol. 29, pp. 2341 to 2350 (1964).
Beyer et al., Chem. Ber, vol. 90, pp. 592-598 (1957).
Houben-Weyl, Methoden der Organischen Chemie, Band IV (5th Ed.), part 2, p. 54 (1955).

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