Hydrochloric Acid → 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

HRID 34412

Reaction equation

HRID 34412 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[NH:5][C:6]([CH3:30])=[C:7]([C:23]([O:25][CH2:26]CC#N)=[O:24])[CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:9]=1[C:10]([O:12]C)=[O:11].C(Cl)Cl.Cl>CC(C)=O>[CH3:30][C:6]1[NH:5][C:4]([CH3:3])=[C:9]([C:10]([OH:12])=[O:11])[CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 109160093,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-cyanoethyl) 5-methyl ester

Product 1

HCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Next, a solution of NaOH (41.3 mL of 35% NaOH in 375 mL H2O) was slowly added to a solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-cyano)ethoxycarbonyl-1,4-dihydropyridine (80 g, 0.21 mol) in acetone (240 mL). Then, CH2Cl2 (500 mL) was added and 12N HCl (41.3 mL) slowly introduced. The resulting precipitate was filtered and recrystallized from dimethylformamide/H2O (175 mL DMF, 72 mL H2O) to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine (mp=242° C.).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customrecrystallized from dimethylformamide/H2O (175 mL DMF, 72 mL H2O)

Sources & evidence

ORD record
ord-edbf78708faf4c909cf5147bfc5e8c4b
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Linked notes

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