Claims
- 1. The process which comprises reacting pyridinylmethyl lower-alkyl ketone of the formula ##STR4## with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone of the formula ##STR5## reacting said ketone with cyanoacetamide or malonamide in the presence of a basic condensing agent and neutralizing the reaction mixture to produce 1,2-dihydro-6-R-2-oxo-5-PY-nicotinonitrile or 1,2-dihydro-6-R-2-oxo-5-PY-nicotinamide of the formula ##STR6## where R and R' are each lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and Q is cyano or carbamyl.
- 2. The process according to claim 1 where 4(or 3)-pyridinylmethyl methyl(or ethyl) ketone is first reacted with triethyl or trimethyl orthoformate, acetic anhydride and acetic acid to produce 2-(ethoxy or methoxy)-1-(4- or 3-pyridinyl)ethenyl methyl(or ethyl) ketone, the latter ketone is next reacted with cyanoacetamide in the presence of at least a molar equivalent quantity of alkali hydroxide per mole of cyanoacetamide in a lower alkanol and then the reaction mixture is neutralized to produce 1,2-dihydro-6-methyl(or ethyl)-2-oxo-5-[4(or 3)-pyridinyl]nicotinonitrile.
- 3. The process according to claim 2 where 4-pyridinylmethyl methyl ketone is first reacted with triethyl orthoformate, acetic anhydride and acetic acid to produce 2-ethoxy-1-(4-pyridinyl)ethenyl methyl ketone, said latter ketone is reacted with cyanoacetamide in the presence of at least a molar equivalent quantity of sodium hydroxide per mole of cyanoacetamide in methanol and the reaction mixture is neutralized to produce 1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinonitrile.
- 4. The process which comprises reacting 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone of the formula ##STR7## with cyanoacetamide or malonamide in the presence of a basic condensing agent and neutralizing the reaction mixture to produce 1,2-dihydro-6-R-2-oxo-5-PY-nicotinonitrile or 1,2-dihydro-6-R-2-oxo-5-PY-nicotinamide of the formula ##STR8## where R and R' are each lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and Q is cyano or carbamyl.
- 5. The process according to claim 4 where 2-(ethoxy or methoxy)-1-(4- or 3-pyridinyl)ethenyl methyl(or ethyl) ketone is reacted with cyanoacetamide in the presence of at least a molar equivalent quantity of alkali hydroxide per mole of cyanoacetamide in a lower alkanol and then the reaction mixture is neutralized to produce 1,2-dihydro-6-methyl(or ethyl)-2-oxo-5-[4(or 3)-pyridinyl]nicotinonitrile.
- 6. The process according to claim 4 where 2-ethoxy-1-(4-pyridinyl)ethenyl methyl ketone is reacted with cyanoacetamide in the presence of at least a molar equivalent quantity of sodium hydroxide per mole of cyanoacetamide in methanol and the reaction mixture is neutralized to produce 1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinonitrile.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of copending U.S. patent application Ser. No. 381,162, filed May 24, 1982 now U.S. Pat. No. 4,417,054.
US Referenced Citations (6)
Non-Patent Literature Citations (1)
Entry |
Mezheritskii et al., Russian Chemical Reviews 42 (5), 392, 399-402 and 410 (1973). |
Continuation in Parts (1)
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Number |
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Country |
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381162 |
May 1982 |
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