Claims
- 1. A process for the production of a compound of the Formula I: ##STR22## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represent hydrogen, hydroxy, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halogen or phenyl; and X represents carboxamido, which comprises:
- A. treating a compound of the Formula II: ##STR23## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above in Formula I with an acid chloride or an acid anhydride to convert all free hydroxyl groups to acyloxy groups and obtain a compound of the Formula III: ##STR24## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 each represent hydrogen, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkanoyloxy of 2 to 6 carbon atoms, halogen, or phenyl; and R.sub.5 represents 1 to 5 carbon lower alkyl;
- B. treating Compound III with a reagent selected from the group consisting of thionyl chloride, oxalyl chloride, and phophorous pentachloride to obtain a compound of the Formula IV: ##STR25## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are as defined above in formula III;
- C. treating a solution of Compound IV with malononitrile in the presence of a basic catalyst selected from the group consisting of triethylamine, alkali metal hydrides, alkali metal hydroxides, amides of the formula M--NH.sub.2 wherein M is an alkali metal, and alkoxides of the formula R--O--M wherein R is a 1 to 6 carbon lower alkyl group and M is an alkali metal, to obtain a compound of the formula: ##STR26## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above in Formula I, which is subjected to acid catalysed hydrolysis to obtain Compound I wherein X is carboxamido.
- 2. A process according to claim 1 wherein, in Step A, an acid derivative selected from the group consisting of acetyl chloride and acetic anhydride is used.
- 3. A process according to claim 1 wherein, in Step C, the solvent is selected from the group consisting of water, benzene, toluene, tetrahydrofuran and dimethylformamide.
- 4. A process according to claim 1 wherein, in Step C, an aqueous solution of sodium hydroxide is used as the solvent and the basic catalyst.
- 5. A process for the production of a compound of the Formula I: ##STR27## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 each represent hydrogen, hydroxy, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halogen or phenyl; and X represents cyano, which comprises:
- A. treating a compound of the formula II: ##STR28## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above in Formula I with an acid chloride or an acid anhydride to convert all free hydroxyl groups to acyloxy groups and obtain a compound of the Formula III: ##STR29## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 each represent hydrogen, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkanoyloxy of 2 to 6 carbon atoms, halogen, or phenyl; and R.sub.5 represents 1 to 5 carbon lower alkyl;
- B. treating Compound III with a reagent selected from the group consisting of thionyl chloride, oxalyl chloride, and phophorous pentachloride to obtain a compound of the Formula IV: ##STR30## wherein R.sub.1, R.sub.2, R.sub.3 , R.sub.4, and R.sub.5 are as defined above in Formula III;
- C. treating a solution of Compound IV with malononitrile in the presence of a basic catalyst selected from the group consisting of triethylamine, alkali metal hydrides, alkali metal hydroxides, amides of the formula M--NH.sub.2 wherein M is an alkali metal, and alkoxides of the formula R--O--M wherein R is a 1 to 6 carbon lower alkyl group and M is an alkali metal, to obtain Compound I wherein X is cyano.
Parent Case Info
This is division of application Ser. No. 532,417, filed Dec. 13, 1974, now U.S. Pat. No. 3,932,466, published Jan. 13, 1976.
US Referenced Citations (5)
Divisions (1)
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Number |
Date |
Country |
Parent |
532417 |
Dec 1974 |
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