2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones

Details 2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones 2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones

1982-05-24

1983-11-22

Jiles, Henry R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546249, C07D21382, C07D21385, C07D21350

Patent

active

044170548

ABSTRACT:
One aspect of the invention resides in the three step process for preparing cardiotonically active 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles (III, Q is CN) or 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinamides (III, Q is CONH.sub.2) which comprises reacting a pyridinylmethyl lower-alkyl ketone (I) with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone (II), reacting II with cyanoacetamide or malonamide in the presence of a basic condensing agent and neutralizing the reaction mixture, where pyridinyl is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents. Other aspects of the invention resides in the intermediate 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones (II) and its two step conversion, as described above, to said compounds (III, Q is CN or CONH.sub.2).

REFERENCES:
patent: 2824121 (1958-02-01), Nicholl et al.
patent: 4223149 (1980-09-01), Opalka et al.
patent: 4276293 (1981-06-01), Lesher et al.
patent: 4313951 (1982-02-01), Lesher et al.
Mezheritskii et al., Russian Chemical Reviews 42 (5), 392, 399-402 and 410 (1973).

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