3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, 3-methyl 5-(2-methylpropyl)ester

The IUPAC name of Nisoldipine is 3-O-methyl 5-O-(2-methylpropyl)2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. With the CAS registry number 63675-72-9, it is also named as 1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester. The product's categories are Active Pharmaceutical Ingredients; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Calcium Channel. Besides, it is light tan crystals, which should be stored in sealed containers in a cool, dry place away from oxidizing agents. In addition, its molecular formula is C₂₀H₂₄N₂O₆ and molecular weight is 388.42.

The other characteristics of this product can be summarized as: (1)EINECS: 264-407-7; (2)ACD/LogP: 4.38; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 4.38; (5)ACD/LogD (pH 7.4): 4.38; (6)ACD/BCF (pH 5.5): 1244.48; (7)ACD/BCF (pH 7.4): 1246.28; (8)ACD/KOC (pH 5.5): 5712.31; (9)ACD/KOC (pH 7.4): 5720.55; (10)#H bond acceptors: 8; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 8; (13)Index of Refraction: 1.544; (14)Molar Refractivity: 101.76 cm³; (15)Molar Volume: 322.1 cm³; (16)Surface Tension: 43.5 dyne/cm; (17)Density: 1.205 g/cm³; (18)Flash Point: 258.2 °C; (19)Melting Point: 147-148 °C; (20)Water Solubility: 24.6 mg/L at 25 °C; (21)Enthalpy of Vaporization: 77.25 kJ/mol; (22)Boiling Point: 503.3 °C at 760 mmHg; (23)Vapour Pressure: 2.95E-10 mmHg at 25 °C.

Preparation of Nisoldipine: frist, you can use o-Nitrobenzaldehyde to react with Isobutyl acetoacetate. And then use the resultant to react with Methyl 3-amino-2-butenoate by heating for 20 hours.

Uses of Nisoldipine: this chemical is a calcium channel blocker of the dihydropyridine class that acts as a potent arterial vasodilator and antihypertensive agent. It is also effective in patients with cardiac failure and angina. Similarly, it can be used to produce 2,6-Dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester.



This reaction needs 20percent aq. HNO₃ at temperature of 100 °C for 1 hour. The yield is 63 %.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(OCC(C)C)\C1=C(\N/C(=C(/C(=O)OC)C1c2ccccc2[N+]([O-])=O)C)C
(2)InChI: InChI=1/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
(3)InChIKey: VKQFCGNPDRICFG-UHFFFAOYAI

The toxicity data is as follows: