Ethanol → 5-Methoxy-4-nitroindole-2-carboxylic acid

HRID 1791829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791829
[OH:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13]CC)=[O:12])=[CH:5]2.[OH-].[K+].[CH2:21](O)C>O>[CH3:21][O:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22030612Ethyl 5-hydroxy-4-nitroindole-2-carboxylate

Produkt 1

HCID 220308175-Methoxy-4-nitroindole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 5-hydroxy-4-nitroindole-2-carboxylate (1.0 g, 3.8 mmol.) was suspended in a mixture of ethanol (20 ml) and water (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 in vacuo and the residue re-dissolved in water (25 ml). The pH was adjusted to pH2 using aqueous hydrochloric acid (2M). The resulting precipitate was filtered off, washed with water and dried in vacuo to give 5-methoxy-4-nitroindole-2-carboxylic acid (790 mg). This was used without further purification.

Aufarbeitung

  1. temperaturethen cooled to ambient temperature
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue re-dissolved in water (25 ml)
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1145bac0a8ef4d079a9ef6503c24f277
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074800B1

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