Potassium Iodide → 2-Iodomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

HRID 1904580Notes

Reaction equation

HRID 1904580 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[I-:29].[K+]>CC(C)=O>[I:29][CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 3064723Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 200374752-Iodomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridineYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-chlorometyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (0.5 g) and potassium iodide (1 g) in acetone (5 ml) is stirred at room temperature for 24 hours, then it is filtered, concentrated under reduced pressure and the residue purified by column chromatography on silica gel (20 g, eluent: hexane/AcOEt 80/20) to give 0.22 g of 2-iodomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine as an oil.

Workup

  1. filtrationit is filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel (20 g, eluent: hexane/AcOEt 80/20)

Sources & evidence

ORD record
ord-9b3be743995741288858057a4df6200a
Source dataset
uspto-grants-1989_06
Patent number
US04839348

Reaction notes

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