1,2-Dihydro-2-oxo-6-(2,2-dimethylpropyl)-3-pyridinecarboxylic acid, analogues, and derivatives. A new class of oral hypoglycemic agents.

1,2-Dihydro-2-oxo-6-(2-methylpropyl)-3-pyridinecarboxylic acid was found to be a hypoglycemic agent but not to have the undesirable mechanism of action possessed by nicotinic acid. A series of 1,2-dihydro-2-oxo-3-pyridinecarboxylic acids with a substituent primarily at the 6-position was prepared by hydrolysis of the corresponding nitriles. The nitriles were prepared by reaction of the sodium enolate of the appropriate 3-substituted 3-oxopropionaldehyde with cyanoacetamide.

New compounds: synthesis of O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine hydrochloride.

Reaction of 2,3,4,5,6-pentafluorobenzyl bromide with N-hydroxyphthalimide produced N-(2,3,4,5,6-pentafluorobenzyloxy)phthalimide which, after hydrazinolysis and treatment with hydrogen chloride, yielded O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine hydrochloride. The latter compound was used to derivatize keto steroids for their analysis by electron-capture GLC.