Hydrochloric Acid → 5-cyano-1H-indole-2-carboxylic Acid

HRID 651156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 651156
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]#[N:16])=[CH:10][CH:9]=2)=[O:5])C.C(O)C.[OH-].[K+].Cl>O>[C:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)#[N:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 4714953Ethyl 5-cyanoindole-2-carboxylate

Produkt 1

HCID 71446255-cyano-1H-indole-2-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Cyano-1H-indole-2-carboxylic acid ethyl ester (1.71 g, 8.0 mmol) was added to a solution of ethanol (10 mL) and potassium hydroxide (2 g) and the resulting mixture heated at reflux for 1 hour. Water was added to dissolve the precipitate, and 6N HCl was added to bring the pH to 1. The mixture was cooled in an ice bath, filtered, and the resulting colorless solid washed with cold water and dried (1.51 g). A portion (1.4 g) was suspended in hot acetic acid (40 mL) and cooled giving a solid which was filtered, washed with cold ethyl acetate and dried: Yield 980 mg 70%; HPLC (60/40) 3.09 minutes (97%).

Aufarbeitung

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 1 hour
  3. additionwas added
  4. temperatureThe mixture was cooled in an ice bath
  5. filtrationfiltered
  6. washthe resulting colorless solid washed with cold water
  7. customdried (1.51 g)
  8. temperaturecooled
  9. customgiving a solid which
  10. filtrationwas filtered
  11. washwashed with cold ethyl acetate
  12. customdried
  13. customHPLC (60/40) 3.09 minutes (97%)

Quellen und Nachweise

ORD-Eintrag
ord-c727cd986b5f4505a85a351047d16623
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277877B1

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