Tetrahydrofuran → 4'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-phenyl)-amide

HRID 2228937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2228937
C([O-])=O.[NH4+].[N+:5]([C:8]1[CH:9]=[C:10]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1)([O-])=O.C1COCC1>[OH-].[OH-].[Pd+2].C(O)(C)C.C(OCC)(=O)C>[NH2:5][C:8]1[CH:9]=[C:10]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:11]=[CH:12][CH:13]=1

Komponenten

7

Edukt 3

HCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 101569574'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amide

Produkt 1

HCID 99248284'-Trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-phenyl)-amideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ammonium formate (16.3 g, 258 mmol, 3 equiv), followed by Pearlman's catalyst [Pd(OH)2] (6.03 g, 4.30 mmol, 0.05 equiv) was added to a solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid (3-nitro-phenyl)-amide (33.2 g, 85.9 mmol, 1 equiv) in isopropanol (330 mL, 10 volumes) and ethyl acetate (170 mL, 5 volumes). The mixture was heated at reflux for 3 hours. After cooling, THF (500 mL) was added to the reaction mixture to help solublize the product. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated to about 100 mL. Ethyl acetate (600 mL) and THF (200 mL) were added. The organic layer was washed with saturated sodium bicarbonate solution (300 mL), dried over sodium sulfate, filtered, and concentrated to afford 4′-trifluoromethyl-biphenyl-2-carboxylic acid (3-amino-phenyl)-amide (28.7 g, 94%) as an off white solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationThe reaction mixture was filtered through diatomaceous earth
  5. concentrationthe filtrate was concentrated to about 100 mL
  6. additionEthyl acetate (600 mL) and THF (200 mL) were added
  7. washThe organic layer was washed with saturated sodium bicarbonate solution (300 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-196049706728420f9b3395c4ae10ba14
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06417367B1

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