Lithium iodide → N-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylic acid

HRID 1582647노트

반응식

HRID 1582647 반응식
[I-].[Li+].C[O:4][C:5]([C:7]1[N:8]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)(=[O:19])=[O:18])[C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([OH:16])=[CH:11][CH:10]=2)=[O:6]>N1C=CC=CC=1>[Cl:27][C:22]1[CH:21]=[C:20]([S:17]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([OH:16])=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:5]([OH:6])=[O:4])(=[O:18])=[O:19])[CH:25]=[CH:24][C:23]=1[Cl:26]

참가 물질

4

반응물 2

HCID 66321Lithium iodideHCID 22718735Methyl n-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylate

생성물 1

HCID 9843144N-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylic acid수율 29%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of anhydrous lithium iodide (870 mg) and methyl_N-(3,4-dichlorophenylsulphonyl)-5-hydroxyindole-2-carboxylate (260 mg) in pyridine (15 ml) was stirred at reflux for 4 hours. The reaction was cooled and concentrated in vacuo. The residue was dissolved in water (20 ml) and acidified with acetic acid. The product was extracted with ethyl acetate and the combined extracts were dried, concentrated in vacuo and the residue purified by column chromatography using dichloromethane-50% ethyl acetate containing 1% acetic acid as eluent to give the desired product as a glass (72 mg, 29%). NMR: δ 6.9 (m, 2H), 7.25 (s, 1H), 7.85 (d, 1H), 7.9 (m, 2H), 8.15 (s, 1H), 9.5 (s, 1H); m/z 385.8 (M−H−). The starting material was prepared by

후처리

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water (20 ml)
  5. extractionThe product was extracted with ethyl acetate
  6. customthe combined extracts were dried
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by column chromatography

출처 및 근거

ORD 기록
ord-9c198956fc244bcbaeac42e96b8c3240
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737435B1

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