Process for the production of 4-amino-6-hydroxy-3-phenyl isoxazo

Details Process for the production of 4-amino-6-hydroxy-3-phenyl isoxazo Process for the production of 4-amino-6-hydroxy-3-phenyl isoxazo

1980-11-21

1982-09-21

Ford, John M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D49804

Patent

active

043508162

ABSTRACT:
Process for the production of 4-amino-6-hydroxy-3-aryl isoxazolo [5,4-b] pyridine-5-carbonitriles having the formula: ##STR1## wherein R (a) is --H, (b) is --Cl or (c) is --CH.sub.3. 3-Amino-2,4,dicyanocrotonic acid methyl ester having the formula: ##STR2## is reacted with a benzohydroxyamino acid chloride having the formula: ##STR3## wherein R has the same meaning as above, in the presence of a strong base (at least molar) at a temperature of up to 10.degree. C. to produce, as an intermediate, the corresponding 3-amino-2-cyano-3-(5-amino-3-aryl-isoxazol-4-yl)-acrylic acid methyl ester having the formula ##STR4## wherein R has the same meaning as above. The intermediate product is reacted in excess diluted NaOH or KOH at a temperature of 50.degree. to 110.degree. C. to produce the corresponding 4-amino-6-hydroxy-3-aryl-isoxazolo [5,4-b] pyridine-5-carbonitrile.

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