Acetic Anhydride → HCID 22174840, Verbindung

HRID 1797066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797066
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:20]=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].[OH-].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]([C:21](=[O:23])[CH3:22])=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:18])([F:17])[F:19])=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 99217692-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)PYRAZOLO[1,5-A]PYRIDINE

Produkt 1

HCID 22174840HCID 22174840, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Versuchsvorschrift

To a mixture of 2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridine (10.30 g, 36.76 mmol) and acetic anhydride (100 mL) was added conc. sulfuric acid (10 drops) and the mixture was stirred and heated at reflux for 1 hour. The reaction mixture was cooled to room temperature and poured into ice water (300 mL). 2N Aqueous sodium hydroxide solution was added to raise the pH of the solution to about 10 and the resulting orange precipitate was collected by filtration. The solid was washed with water, air-dried, and then dried under vacuum to afford the title compound as an orange solid, 11.87 g (quant.). 1H NMR (DMSO-d6): δ 9.58 (s, 1H), 8.41 (d, 1H, J=9.3 Hz), 7.89 (d, 1H, J=9.5 Hz), 7.74 (m, 2H), 7.39 (m, 2H), 2.22 (s, 3H). MS (ES) 323 (M+1).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureto raise the pH of the solution to about 10
  4. filtrationthe resulting orange precipitate was collected by filtration
  5. washThe solid was washed with water
  6. customair-dried
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d57b3fa1146e44eba063e1322e6e8da0
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034030B2

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