Certain 2-substituted-6-(3 or 4-pyridyl)-nicotinic acid derivatives

Abstract

Abstract INTERMEDIATE 2-R1 NH-6-Q''''''-NICOTINIC ACID (V''), WHERE R1 IS LOWER-ALKYL AND Q'''''' IS 4(OR 3) -PYRIDYL OR 4(OR 3)PYRIDYL HAVING ONE OR TWO LOWER-ALKYL SUBSTITUENTS, IS PREPARED IN THE THREE STEPS OF: HYDROLYZING 1,2-DIHYDRO-2OXO-6-Q''''''-NICOTINONITRILE (VII)TO PRODUCE 1,2-DIHYDRO-2 OXO-6-Q''''''-NICOTINIC ACID (VIII), HALOGENATING VIII TO PRODUCE 2-HALO-6Q''''''-NICOTINIC ACID (VI''), AND, REACTING VI'' WITH R1NH2 TO PRODUCE V''. ALSO SHOWN ARE THE STEPS OF: REACTING 2-HALO-6-Q''''-NICOTINIC ACID (VI''), AND, REACTING IS AS Q'''''' AND ALSO LOWER-ALKYL, TO PRODUCE 2-R1 NH-6-Q''''NICOTINIC ACID (V), HEATING V WITH A LOWER-ALKYL CHLOROFORMATE OR PHOSGENE TO PRODUCE 1-R1-7-Q''''-1H,4H-PYRIDO(2,3-D)(1,3) OXAZINE-2,4-DIONE (I''), CONVERTING I'' WHERE Q'''' IS CH3 TO ITS 8-OXIDE AND REACTING THE 8-OXIDE WITH A LOWER -ALKANOIC ACID ANHYDRIDE TO PRODUCE I WHERE 7-CH3 IS CONVERTED TO 7-(LOWER-ALKANOYLOYMETHYL), REACTING 1 -R1 -7-Q-1H,4H-PRIDO(2,3-D)(1,3)OXAZINE-2,4-DIONE, WHERE Q IS AS Q'''' AND ALSO LOWER-ALKANOYLOXYMETHYL, WITH R2-C(=O)CH2COOR, WHERE R2 IS H OR CH3 AND R IS LOWER-ALKYL, TO PRODUCE LOWER-ALKYL 1-R1-1,4-DIHYDRO-2R2-4-OXO-7-Q-1,8-NAPHTHYRIDINE-3-CARBOXYLATE (III), AND, HYDROLYZING III TO OBTIN 1-R,1,4-DIHYDRO-2-R2-4-OXO-7Q''-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID (IV), WHERE Q'' IS LIKE Q BUT HAVING HYDROXYMETHYL IN PLACE OF LOWERALKANOYLOXYMETHYL.

Inventors

• 👤 R Brundage
• 👤 G Lesher

Bibliographic Details