Process for the preparation of 5-chloro and 5-bromo-2-hydroxynic

Details Process for the preparation of 5-chloro and 5-bromo-2-hydroxynic Process for the preparation of 5-chloro and 5-bromo-2-hydroxynic

1987-11-13

1990-10-02

Ford, John M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546296, 546345, C07D21372, C07D21361

Patent

active

049608967

ABSTRACT:
A process for the preparation of 5-halo-2-hydroxynicotinic acids having the formula: ##STR1## wherein X is chlorine or bromine, Y and Z are selected from hydrogen, loweralkyl or loweralkyl, is described wherein a corresponding 2-hydroxynicotinic acid is halogenated with alkali-metal hypohalite in a strongly alkaline solution pH 12 and above. Certain aspects of the isolation of the product are directed to avoiding replacement of the carboxy group with halogen.

REFERENCES:
patent: 4716281 (1987-12-01), Goddard
Fieser's Reagent for Org. Synthesis, vol. 5, p. 322 (1975) and vol. 6, p. 543 (1977).
Klingsberg, Heterocyclic Compounds-Pyridine and its Derivatives, Part III (1966) pp. 646-659.
Morrison et al., Org. Chem. 3rd Ed., pp. 1013-1014.
Bachman et al., J. Am. Chem. Soc. 70, 238(1948) pp. 2381-2384.
Klingsberg, Heterocyclic Compounds-Pyridine and its Derivatives, Part II (1961) pp. 306-310.

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