4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.

4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.

A method of forming a compound of formula (I) is provided. Some embodiments of the compound of formula (I) are known to have herbicidal activity.

##STR00001##

The method comprises combining a compound of formula (II) and a compound of formula (IIIa) or (IIIb), or a salt or ester thereof:

##STR00002##

in a liquid mixture comprising the compounds of formula (II), formula (IIIa) or (IIIb), water, a non-aqueous solvent, a surfactant, a catalyst, and a ligand at certain temperature, pH, and HLB ranges to form a chemical reaction product mixture comprising the compound of formula (I) and by-products.

A method of forming a compound of formula (I) is provided. Some embodiments of the compound of formula (I) are known to have herbicidal activity.

##STR00001##

The method comprises combining a compound of formula (II) and a compound of formula (IIIa) or (IIIb), or a salt or ester thereof:

##STR00002##

in a liquid mixture comprising the compounds of formula (II), formula (IIIa) or (IIIb), water, a non-aqueous solvent, a surfactant, a catalyst, and a ligand at certain temperature, pH, and HLB ranges to form a chemical reaction product mixture comprising the compound of formula (I) and by-products.

The present disclosure generally relates to methods of preparing nicotine and resolving R,S nicotine to enrich the (S)(−) enantiomer. The method may comprise combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a strong base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof; and reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na.sub.2S.sub.2O.sub.4 to produce racemic nicotine or salt thereof. Resolving the racemic nicotine (or other enantiomeric mixture) may comprise combining the nicotine with (−)-O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA).

Disclosed are processes for preparing [(3-hydroxypyridine-2-carbonyl)amino]-alkanoic acids, derivatives, inter alia, 5-aryl substituted and 5-heteroaryl substituted [(3-hydroxypyridine-2-carbonyl]amino}acetic acids. Further disclosed are methods for making prodrugs of [(3-hydroxypyridine-2-carbonyl)-amino]acetic acids, for example, {[(3-hydroxypyridine-2-carbonyl]amino}acetic acid esters and {[3-hydroxypyridine-2-carbonyl]amino}acetic acid amides. The disclosed compounds are useful as prolyl hydroxylase inhibittors or for treating conditions wherein prolyl hydroxylase inhibition is desired.

Disclosed are processes for preparing [(3-hydroxypyridine-2-carbonyl)amino]-alkanoic acids, derivatives, inter alia, 5-aryl substituted and 5-heteroaryl substituted [(3-hydroxypyridine-2-carbonyl]amino}acetic acids. Further disclosed are methods for making prodrugs of [(3-hydroxypyridine-2-carbonyl)-amino]acetic acids, for example, {[(3-hydroxypyridine-2-carbonyl]amino}acetic acid esters and {[3-hydroxypyridine-2-carbonyl]amino}acetic acid amides. The disclosed compounds are useful as prolyl hydroxylase inhibittors or for treating conditions wherein prolyl hydroxylase inhibition is desired.

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction.

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction.

The invention relates to a method for (I) producing a carboxylic ester of formula (I). Said method comprises the steps of: a) bringing an organosilane/borane of formula Si or B into contact with CO.sub.2, in the presence of a catalyst and an electrophilic compound of formula (III), the groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Y, and M′ being as defined in claim 1; and optionally b) recovering the compound of formula (I) produced.

##STR00001##