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

HRID 1458907Notes

Reaction equation

HRID 1458907 reaction equation
[I-:1].[Na+].Cl[CH2:4][C:5]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:12]2[C:7](=[CH:8][C:9]([O:32][CH3:33])=[C:10]([O:30][CH3:31])[CH:11]=2)[N:6]=1>C(C(C)=O)C>[CH3:29][O:28][C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][C:23]=1[O:26][CH3:27])[N:6]=[C:5]([CH2:4][I:1])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]2[C:12]1[CH:7]=[CH:8][C:9]([O:32][CH3:33])=[C:10]([O:30][CH3:31])[CH:11]=1

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 58.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium iodide (1.68 g) and methyl ethyl ketone (15 ml) was stirred at 80° C. for 1 hour, and then ethyl 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (2.0 g) was added thereto, and the resulting mixture was stirred at the same temperature for 12 hours. The insoluble solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (1/1,v/v) gave ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-iodomethylquinoline-3-carboxylate (1.4 g, 58%) which was then recrystallized from ethyl acetate-hexane.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 12 hours
  2. filtrationThe insoluble solid was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was poured into water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated
  9. washThe fractions eluted with chloroform/ethyl acetate (1/1,v/v)

Sources & evidence

ORD record
ord-1436e882ba40470d8f61049e3c5d1d6e
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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