Isonicotinic Acid → HCID 86651051, Verbindung

HRID 884947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884947
CCN=C=NCCCN(C)C.[C:12]([OH:20])(=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[NH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:37])([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:24][C:23]=1[OH:38]>N1C=CC=CC=1>[OH:38][C:23]1[CH:24]=[CH:25][C:26]([C:28]([F:37])([C:29]([F:30])([F:31])[F:32])[C:33]([F:34])([F:35])[F:36])=[CH:27][C:22]=1[NH:21][C:12](=[O:20])[C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 5922Isonicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 866510652-Amino-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenol

Produkt 1

HCID 86651051HCID 86651051, VerbindungAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of 0.58 g of WSC and 5 ml of pyridine, 0.37 g of isonicotinic acid was added. The reaction mixture was stirred at room temperature for 25 minutes. To the reaction mixture, 0.75 g of 2-amino-4-(heptafluoroisopropyl)phenol was added and was stirred while heating at 60° C. for three hours. The mixture was cooled to room temperature, and then concentrated under reduced pressure. Then, water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.79 g of N-[2-hydroxy-5-(heptafluoroisopropyl)phenyl]isonicotinamide.

Aufarbeitung

  1. additionwas added
  2. stirringwas stirred
  3. temperaturewhile heating at 60° C. for three hours
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionThen, water was added to the residue
  7. extractionfollowed by extraction with ethyl acetate twice
  8. washThe combined organic layers were washed with water
  9. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2b1c510b6f784c789f11d78da80a874b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242133B2

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