Hydrochloric Acid → 2,6-Dimethyl-4-(4-nitrophenyl)-5-[(3-phenyl-2-propene-1-yl)carbamoyl]-1,4-dihydropyridine-3-carboxylic acid

HRID 1700348Notes

Reaction equation

HRID 1700348 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:24](=[O:35])[NH:25][CH2:26][CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[C:7]=1[C:8]([O:10]CCC#N)=[O:9].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:24](=[O:35])[NH:25][CH2:26][CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]([C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 701576352-Cyanoethyl 2,6-dimethyl-4-(4-nitrophenyl)-5-[(3-phenyl-2-propene-1-yl)carbamoyl]-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 701561442,6-Dimethyl-4-(4-nitrophenyl)-5-[(3-phenyl-2-propene-1-yl)carbamoyl]-1,4-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

396 mg (0.814 mmol) of 2-cyanoethyl 2,6-dimethyl-4-(4-nitrophenyl)-5-[(3-phenyl-2-propene-1-yl)carbamoyl]-1,4-dihydropyridine-3-carboxylate was dissolved in 10 ml of methanol. 0.895 ml of 1 N aqueous sodium hydroxide solution was added to the solution, and they were stirred at room temperature overnight. 1 N hydrochloric acid was added to the reaction mixture and then methanol was evaporated under reduced pressure. Water was added to the residue, and a precipitate thus obtained was taken by the filtration. The product was washed with water and then with hexane/ethyl acetate (3:1) and dried under reduced pressure to obtain the title compound.

Workup

  1. custommethanol was evaporated under reduced pressure
  2. additionWater was added to the residue
  3. customa precipitate thus obtained
  4. filtrationwas taken by the filtration
  5. washThe product was washed with water
  6. dry with materialwith hexane/ethyl acetate (3:1) and dried under reduced pressure

Sources & evidence

ORD record
ord-baa74793c63542f5838ed5784e74f4f3
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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