Lithium Hydroxide → 6-Chloro-1H-indole-5-carboxylic acid

HRID 1976779ノート

反応式

HRID 1976779 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([O:13]C)=[O:12].[Li+].[OH-].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 10727132Methyl 6-chloro-1H-indole-5-carboxylate

生成物 1

HCID 225574516-Chloro-1H-indole-5-carboxylic acid収率 60.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A solution of Example 58B (1.17 g, approximately 5.6 mmol) in THF (50 mL) was treated with 1M LiOH (56 mL, 56 mmol), heated at 50° C., stirred for 18 hours, treated with 1M NaOH, washed with diethyl ether, acidified with HCl, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified on silica gel with 50% ethyl acetate/hexanes to provide of 660 mg of the desired product.

後処理

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified on silica gel with 50% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-83e1b6ba1eb343189e593abfa557bec4
出典データセット
uspto-grants-2001_05
特許番号
US06228868B1

反応ノート

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