Ethanol → 4-Bromo-5-methoxy-1H-indole-2-carboxylic acid

HRID 1791803노트

반응식

HRID 1791803 반응식
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.[OH-].[K+].[CH2:19](O)C>O>[Br:1][C:2]1[C:10]([O:11][CH3:19])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[NH:6]2

참가 물질

5

반응물 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22030665Ethyl 4-bromo-5-hydroxyindole-2-carboxylate

생성물 1

HCID 133565154-Bromo-5-methoxy-1H-indole-2-carboxylic acid수율 96%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

Ethyl 4-bromo-5-hydroxyindole-2-carboxylate (1.49 g, 5 mmol.), (Jnl. Org. Chem. 1984, 49, 4761), was dissolved in ethanol (10 ml) and water (3.5 ml). Potassium hydroxide (840 mg) was added and the mixture stirred at 50° C. under an atmosphere of nitrogen for 1 hour then cooled to ambient temperature. The solvent was evaporated and the residue redissolved in water (25 ml). 2M Aqueous hydrochloric acid was added until the reaction mixture was at pH4, giving a precipitate which was filtered off, washed with water and dried under vacuum to give 4-bromo-5-methoxyindole-2-carboxylic acid (1.30, 96%).

후처리

  1. temperaturethen cooled to ambient temperature
  2. customThe solvent was evaporated
  3. dissolutionthe residue redissolved in water (25 ml)
  4. addition2M Aqueous hydrochloric acid was added until the reaction mixture
  5. customgiving a precipitate which
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-b0cff2d5040b4c34a8d7dbfcf7338615
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074800B1

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