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

HRID 1582647ノート

反応式

HRID 1582647 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-9c198956fc244bcbaeac42e96b8c3240
出典データセット
uspto-grants-2004_05
特許番号
US06737435B1

反応ノート

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