Hydrochloric Acid → 3-Butyl-1-methyl-1H-indole-5-carboxylic acid

HRID 349003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349003
[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]CC)=[O:15])[CH:12]=2)[N:7]([CH3:19])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[N:7]([CH3:19])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21086101Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate

Produkt 1

HCID 210857263-Butyl-1-methyl-1H-indole-5-carboxylic acidAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate (0.294 g) in methanol (20 mL) was added 1N NaOH (10 mL). The mixture was stirred at 50° C. for 18 h, cooled to room temperature and poured into 1N HCl (50 mL). The mixture was extracted with ethyl acetate and the ethyl acetate extract was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give 0.234 g (89%) of the title compound: 1H NMR (CD3OD) δ 0.965, 1.42, 1.69, 2.76, 3.77, 7.02, 7.35, 7.84, 8.29.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionthe ethyl acetate extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d52667a586a34b028296c4edef5fb1e2
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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