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

HRID 617217ノート

反応式

HRID 617217 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a29e968431e34d57b21fce96c04fa55c
出典データセット
uspto-grants-1999_09
特許番号
US05948782

反応ノート

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