Abstract: Apomorphine derivatives are prepared in improved yield by rearrangement of the corresponding morphine derivative in the presence of anhydrous orthophosphoric acid under a partial vacuum and hydrolysis of the resulting phosphate esters in an aqueous medium.

Abstract: Process of reacting 3-PY-aniline (I) with lower-alkyl acetoacetate (II) and tri-(lower-alkyl) orthoformate (III) to produce lower-alkyl .alpha.-(3-PY-anilinomethylene)acetoacetate (IV), heating lower-alkyl .alpha.-(3-PY-anilinomethylene)acetoacetate (IV), to produce 3-acetyl-1,4-dihydro-4-oxo-7-PY-quinoline (V) which is tautomeric with 3-acetyl-4-hydroxy-7-PY-quinoline (VA), reacting V (or VA) with a lower-alkylating agent to produce 3-acetyl-1-(lower-alkyl)-1,4-dihydro-4-oxo-7-PY-quinoline (VI) and converting VI to 1-(lower-alkyl)-1,4-dihydro-4-oxo-7-PY-3-quinolinecarboxylic acid (VII), where PY is 4(or 3)-pyridyl or 4(or 3)-pyridyl having one or two lower-alkyl substituents. The compounds of formula VII are known antibacterial agents.

Abstract: Improvements in the reduction of 6-acetamido-2-picoline to produce 6-ethylamino-2-picoline, the improvements being in the use of diborane as the reducing agent and in the use of a low boiling petroleum solvent to separate the soluble 6-ethylamino-2-picoline from the insoluble starting material 6-acetamido-2-picoline. The 6-ethylamino-2-picoline final product is useful as an intermediate in a known method of preparing nalidixic acid, an antibacterial agent.