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

HRID 1976779노트

반응식

HRID 1976779 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 225574516-Chloro-1H-indole-5-carboxylic acid수율 60.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83e1b6ba1eb343189e593abfa557bec4
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06228868B1

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