m-Chloroperbenzoic acid → HCID 70490388, compound

HRID 615135Notes

Reaction equation

HRID 615135 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15]([C:17]1[CH:22]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:20]([CH3:34])[NH:19][C:18]=1[CH3:35])=[O:16])[CH3:13].C([O-])(=O)C.[Na+]>C(Cl)Cl>[CH2:32]([O:31][C:29]([C:21]1[CH:22]([C:23]2[CH:24]=[N+:25]([O-:9])[CH:26]=[CH:27][CH:28]=2)[C:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])=[C:18]([CH3:35])[NH:19][C:20]=1[CH3:34])=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 100279Diethyl 2',6'-dimethyl-1',4'-dihydro[3,4'-bipyridine]-3',5'-dicarboxylateHCID 517045Sodium Acetate

Product 1

HCID 70490388HCID 70490388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.1 g of 3-chloroperbenzoic acid in 40 ml of methylene chloride is added dropwise to a mixture of 3.3 g of 2,6-dimethyl-4-(3-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester and 1.4 g of sodium acetate in 50 ml of methylene chloride. The reaction mixture is stirred at room temperature for 20 hours and extracted with a 2N aqueous sodium carbonate solution and then twice with an aqueous iron(II) sulphate solution. The organic solution is dried and concentrated by evaporation under reduced pressure. The residue is chromatographed over 400 g of silica gel, there being used as liquid phase a 95:5 mixture of chloroform and methanol and the chromatograph being effected by means of thin layer chromatography (silica gel; mobile phase: chloroform/methanol 95:5). The eluate, which contains the main portion of the desired compound, is concentrated by evaporation, and the residue is crystallised from acetonitrile. In this manner, 2,6-dimethyl-4-(1-oxido-3-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is obtained, which melts at 191°-193° and is identical to the product obtainable in accordance with the process of Example 2.

Workup

  1. extractionextracted with a 2N aqueous sodium carbonate solution
  2. customThe organic solution is dried
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue is chromatographed over 400 g of silica gel, there
  5. additiona 95:5 mixture of chloroform and methanol
  6. concentrationis concentrated by evaporation
  7. customthe residue is crystallised from acetonitrile

Sources & evidence

ORD record
ord-925ae6bd56454ab5bbf4bdc3e3243f6c
Source dataset
uspto-grants-1985_02
Patent number
US04497808

Reaction notes

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