Hydrochloric Acid → 9H-Carbazole-3-carboxylic acid

HRID 50615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50615
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].[OH-].[Na+].Cl>CO>[CH:7]1[C:8]2[NH:9][C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[CH:17]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 504069Methyl Carbazole-3-Carboxylate

Produkt 1

HCID 31520239H-Carbazole-3-carboxylic acidAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Carbazole-3-carboxylic acid methyl ester (450 mg) was dissolved in 7 mL of methanol, and the solution was added with 2.5 mL of 2 N aqueous sodium hydroxide, and stirred at 60° C. for 3 hours. Subsequently, the reaction mixture was cooled and then neutralized with hydrochloric acid, and the deposited precipitates were collected to obtain 410 mg of carbazole-3-carboxylic acid. The resulting carbazole-3-carboxylic acid (205 mg), 6-(1-naphthalenesulfonyl)aminopentylamine (292 mg) obtained in the example and WSC (192 mg) were dissolved in 5 mL of DMF and stirred at room temperature for 3 hours. The reaction mixture was added with water and extracted with ethyl acetate. Then, the organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: chloroform/methanol=95/5) to obtain 123 mg of the compound, 3-(1-naphthylsulfonylaminopentylaminocarbonyl)carbazole.

Aufarbeitung

  1. temperatureSubsequently, the reaction mixture was cooled
  2. customthe deposited precipitates
  3. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-eeadd77809b647379514a7885aa47ff6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713473B1

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