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

HRID 1791803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791803
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b0cff2d5040b4c34a8d7dbfcf7338615
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074800B1

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