Sodium Iodide → Ethyl 2-iodomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate

HRID 1584145Notes

Reaction equation

HRID 1584145 reaction equation
[I-:1].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:9]([CH2:32]Cl)=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)=[CH:15][C:14]([O:28][CH3:29])=[C:13]([O:30][CH3:31])[CH:12]=2)=[O:7])[CH3:4]>CC(=O)CC>[CH2:3]([O:5][C:6]([C:8]1[C:9]([CH2:32][I:1])=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)=[CH:15][C:14]([O:28][CH3:29])=[C:13]([O:30][CH3:31])[CH:12]=2)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 21851133Ethyl 2-iodomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium iodide (1.68 g) and 2-butanone (15 ml) was stirred at 80° C. for 1 hour, after which 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylic acid ethyl ester (2.68 g) was added, followed by stirring at 80° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured over water and then extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (1:1, v/v) to yield -6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-iodomethylquinoline-3-carboxylic acid ethyl ester (1.4 g, 58%), which was then recrystallized from ethyl acetate-hexane to yield a colorless prismatic crystal having a melting point of 170 to 171° C.

Workup

  1. stirringby stirring at 80° C. for 12 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured over water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationafter which the solvent was distilled off under reduced pressure
  8. washeluted with chloroform-ethyl acetate (1:1

Sources & evidence

ORD record
ord-d77f2a508ef6468caf8b565a3a78e7ee
Source dataset
uspto-grants-1999_08
Patent number
US05932592

Reaction notes

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