Claims
- 1. The process for preparaing a 3-(pyridinyl)-2-cyclohexen-1-one having the formula ##STR10## where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, which comprises reacting methyl vinyl ketone with lower-alkyl 3-(pyridinyl)-3-oxo-propanoate of the formula ##STR11## where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R is lower-alkyl, in the presence of a basic condensing agent to produce lower-alkyl 5-oxo-2-(pyridinylcarbonyl)hexanoate of the formula ##STR12## heating said hexanoate under aqueous acidic conditions thereby hydrolyzing and decarboxylating it to produce 1-PY-hexan-1,5-dione and reacting said hexan-1,5-dione with a basic condensing agent to produce said 3-PY-2-cylohexen-1-one or first reacting said lower-alkyl 5-oxo-2-(pyridinylcarbonyl)hexanoate with a basic condensing agent to produce lower-alkyl 3-(pyridinyl)-2-cyclohexen-1-one-4-carboxylate and then heating under aqueous acidic conditions to hydrolyze and decarboxylate said 4-carboxylate to produce said 3-(pyridinyl)-2-cyclohexen-1-one.
- 2. The process according to claim 1 where the basic condensing agent is an alkali metal lower-alkoxide in the first step and an aqueous alkali hydroxide solution in the last step.
- 3. The process according to claim 2 where PY is 4-pyridinyl, 3-pyridinyl, 2-methyl-4-pyridinyl or 2-methyl-5-pyridinyl.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a division of copending application Ser. No. 737,392, filed Nov. 1, 1976 now U.S. Pat. No. 4,075,217 , granted Feb. 21, 1978 in turn, a division of its copending application Ser. No. 668,451, filed Mar. 19, 1976 and now U.S. Pat. No. 4,026,900, issued May 31, 1977.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4026900 |
Gelotte et al. |
May 1977 |
|
Non-Patent Literature Citations (6)
Entry |
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). |
Divisions (2)
|
Number |
Date |
Country |
Parent |
737392 |
Nov 1976 |
|
Parent |
668451 |
Mar 1976 |
|