Sodium Hydroxide → 3-bromo-1H-indole-2-carboxylic acid

HRID 2292700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292700
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[Na+]>CCO.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Produkt 1

HCID 23256883-bromo-1H-indole-2-carboxylic acidAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-bromoindole-2-carboxylate (54.40 g, 203 mmol) in EtOH (600 ml) and water (50 ml) with NaOH (20.20 g, 505 mmol) was refluxed for 1 h. The mixture was cooled and the sodium salt of the title compound was removed by filtration. This was acidified (aqueous 3N HCl) and extracted with ethyl acetate. The organic extract was washed with water then brine, dried (sodium sulfate) and concentrated. Crystallization from ethyl acetate afforded the product (47.1 g, 88%). mp 201°-203° C.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customthe sodium salt of the title compound was removed by filtration
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialbrine, dried (sodium sulfate)
  7. concentrationconcentrated
  8. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3dbfb79717d441fd8d38915e8fbb7d05
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684032

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