Hydrochloric Acid → 1-ethyl-1H-indole-3-carboxylic acid

HRID 1372688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372688
[OH-].[Na+].Cl.[CH2:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17]C)=[O:16])=[CH:7]1)[CH3:5]>C1COCC1>[CH2:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([OH:17])=[O:16])=[CH:7]1)[CH3:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 5191495Methyl 1-ethylindole-3-carboxylate

Produkt 1

HCID 36971601-ethyl-1H-indole-3-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In THF (9.0 ml) was dissolved the methyl 1-ethylindole-3-carboxylate obtained in the above-described (Step 1). To the resulting solution was added 0.25N NaOH (9.0 ml) at room temperature. After the reaction mixture was stirred at 50° C. for 36 hours, 1N NaOH (1.0 ml) was added thereto, followed by stirring at 70° C. for 9 hours. The reaction mixture was cooled to room temperature, and then neutralized with 1N HCl (4.5 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 1-ethylindole-3-carboxylic acid (388.0 mg, 90%, yield of 2 steps) as a pale pink amorphous substance.

Aufarbeitung

  1. customobtained in the above-described (Step 1)
  2. stirringby stirring at 70° C. for 9 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washwashed with water
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-af1ffb82734b4e67a4e8e17d95ece895
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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