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

HRID 617217Notes

Reaction equation

HRID 617217 reaction equation
[I-:1].[Na+].Cl[C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:32])=[C:9]([O:29][CH3:30])[CH:10]=2)[N:5]=1.[CH2:33](C(C)=O)C>>[CH3:30][O:29][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:31][CH3:32])[N:5]=[C:4]([CH2:33][I:1])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]2[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 21801288Ethyl 2-chloro-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate

Product 1

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

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. Then ethyl 2-chloro-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (2.0 g) was added, and the resulting mixture was stirred at the same temperature for 12 hours. The insoluble materials were 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 (MgSO4), and the solvent was distilled off. The residual oil was subjected to column chromatography on silica gel. From the fraction eluted with chloroform/ethyl acetate (1:1, v/v), ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-iodomethylquinoline-3-carboxylate (1.4 9, 58%) was obtained and recrystallized from ethyl acetate/hexane.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 12 hours
  2. filtrationThe insoluble materials were 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 (MgSO4)
  8. distillationthe solvent was distilled off
  9. washFrom the fraction eluted with chloroform/ethyl acetate (1:1

Sources & evidence

ORD record
ord-a29e968431e34d57b21fce96c04fa55c
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

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