Potassium Carbonate → HCID 70393634, compound

HRID 620081Notes

Reaction equation

HRID 620081 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([OH:22])=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4].[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43]Br)=[CH:37][CH:36]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([O:22][CH2:43][CH2:42][O:41][C:38]2[CH:37]=[CH:36][C:35]([CH2:34][CH2:33][NH:32][C:30]([O:29][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:31])=[CH:40][CH:39]=2)=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 54155326HCID 54155326, compound

Product 1

HCID 70393634HCID 70393634, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.3 g (100 mmol) of 1,4-dihydro-2.6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-methyl ester, 3.5 g (10 mmol) of the bromoethoxy compound from step 1b), and 2.8 g (20 mmol) of potassium carbonate are heated at boiling in 50 ml of acetonitrile while stirring and under reflux. After approximately 20 hours, the reaction mixture is filtered and the filtrate is concentrated by evaporation under reduced pressure. The residue is dissolved in ethyl acetate and washed with water, and the organic phase is concentrated by evaporation in vacuo. Crude 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-tertiary butoxycarbonylaminoethyl)-phenoxy]-ethyl}-ester 5-methyl ester is thus obtained and is used further in crude form.

Workup

  1. temperatureunder reflux
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated by evaporation under reduced pressure
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water
  6. concentrationthe organic phase is concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-0c7207c7d15645d19fa99e33a43d6c77
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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