74936-76-8

Basic information

• Product Name: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) ester
• Synonyms: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono(2-methoxyethyl) ester(9CI); W 2100
• CAS NO: 74936-76-8
• Molecular Formula: C18H20 N2 O7
• Molecular Weight: 376.366
• Mol File: 74936-76-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) ester(74936-76-8)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) ester(74936-76-8)

Safety Data

• Hazardous Substances Data: 74936-76-8(Hazardous Substances Data)

Upstream product

• 39562-22-6 (E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 
• 22502-03-0 2-methoxyethyl-3-oxobutanoate 
• 75130-29-9 J-6-163 

Relevant articles and documents

Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates

Several 3-(2-cyanoethyl)-1,4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1,4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.

Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing a nitrooxy moiety at the 3-ester position

The synthesis of a new series of dihydropyridines containing a nitrooxy moiety at the 3-ester position is described. The antihypertensive activity of the compounds was examined and compared with that of nifedipine; some of them were relatively potent. The structure-activity relationship is also discussed.

Process for the preparation of 1,4-dihydropyridinedicarboxylic esters

In the preparation of a 1,4-dihydropyridine of the formula STR1 in which R is a phenyl radical which is optionally substituted once or twice by nitro and/or chlorine, R1 is a C1 -C4 -alkyl radical which is optionally substituted by a C1 -C4 -alkoxy group, and R2 is a C1 -C12 -alkyl radical which is optionally substituted by a C1 -C4 -alkoxy group, a trifluoromethyl group or the radical (C6 H5 CH2) (CH3)N, by preparing an ylidene compound of the formula STR2 and reacting such ylidene compound with an enamine compound of the formula STR3 the improvement which comprises preparing the ylidene compound by reaction of a ketocarboxylic ester of the formula STR4 with an aldehyde of the formula RCHO, in a solvent in the presence of a catalytic amount of any acetate salt of an amine, at a temperature from about -10° C. up to 100° C. The products symmetrical or unsymmetrical, are produced in high yield and purity.