Hydrochloric Acid → 1-butyl-4-cyano-1H-indole-6-carboxylic acid

HRID 14181

Reaktionsgleichung

Reaktionsgleichung von HRID 14181
[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([C:18]#[N:19])[CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([C:18]#[N:19])[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21086135Methyl 1-butyl-4-cyano-1H-indole-6-carboxylate

Produkt 1

HCID 210851701-butyl-4-cyano-1H-indole-6-carboxylic acidAusbeute 4,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of methyl 1-butyl-4-cyano-1H-indole-6-carboxylate (10.5 g) in methanol (15 mL) was added 1N NaOH (3.0 mL). The mixture was heated at 40° C. for 2 h then cooled to room temperature. The mixture was poured into 1N HCl and extracted into ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and concentrated to give 0.45 g of the title compound: 1H NMR (CDCl3) δ 0.973, 1.38, 1.88, 4.27, 6.79, 7.48, 8.24, 8.38.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. extractionextracted into ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c3ce087efd184b318578b9500d7aca1a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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