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Dimethylformamide → Acetoxymethyl methyl 4-(2',3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 341866
Notes
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Reaction equation

HRID 341866 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:23])=[C:5](CC(O)=O)[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:7]=1[C:8]([OH:10])=[O:9].[C:24](=[O:27])([OH:26])[O-].[Na+].[C:29]([O:32][CH2:33]Cl)(=[O:31])[CH3:30].[CH3:35]N(C=O)C>>[Cl:18][C:12]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=1[CH:6]1[C:5]([C:24]([O:26][CH3:35])=[O:27])=[C:4]([CH3:23])[NH:3][C:2]([CH3:1])=[C:7]1[C:8]([O:10][CH2:33][O:32][C:29](=[O:31])[CH3:30])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 69366Chloromethyl acetateHCID 516892Sodium BicarbonateHCID 668096561,4-Dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid

Product 1

HCID 70148229Acetoxymethyl methyl 4-(2',3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 48%

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 1 ,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (0.3 g, 0.83 mmol) and sodium bicarbonate (0.14 g, 1.69 mmol) in DMF (15 ml) under nitrogen atmosphere was added chloromethyl acetate (0.137 g, 1.26 mmol). The reaction mixture was heated at 80° C. for 18 h. Workup by evaporation of solvent and addition of water. Extraction with dichloromethane, the extract was dried over sodium sulfate and concentrated. The resulting oil was subjected to flash chromatography [silica gel, dichloromethane - dichloromethane/methanol (9/1) gradient] to give colorless crystals (0.17 g, 48%) mp.144.5°-147.6° C. 1H-NMR (CDCl3): 7.30-7.04 (Ar, 3H); 5.97 (s, 1H); 5.73 (d, J=5.5 Hz, 1H); 5.69 (d, J=5.5 Hz, 1H); 5.46 (s, 1H); 3.60 (s, 3H); 2.32 (s, 3H); 2.30 (s, 3H); 2.03 (s, 3H). 13C-NMR (CDCl3): 169.64; 167.63; 165.81; 147.46; 146.77; 143.85; 132.86; 131.15; 129.83; 128.31; 126.98; 103.97; 101.89; 78.73; 50.93; 38.45; 20.80; 19.86; 19.26.

Workup

  1. customWorkup by evaporation of solvent and addition of water
  2. extractionExtraction with dichloromethane
  3. dry with materialthe extract was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-352bbaa958f64446b35c8aea8d16245a
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05856346

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes