HCID 67291102, Verbindung → 2-(4,4-Dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline

HRID 1036921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036921
[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[CH2:3]1>[Cl-].[NH4+].C(O)C.[Fe]>[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:13])[F:15])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:3]1

Komponenten

5

Edukt 1

HCID 67291102HCID 67291102, Verbindung

Produkt 1

HCID 672899892-(4,4-Dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a suspension of 4,4-dimethyl-2-(2-nitrophenyl)-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline (2.56 g, 7.3 mmol) in saturated aqueous ammonium chloride (20 mL) and ethanol (30 mL) was added iron powder (1.2 g, 21.0 mmol) at room temperature After addition, the resulting mixture was stirred at reflux under Nitrogen for 3 h. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The solvent of ethanol in filtrate was removed under reduced pressure and the water phase was extracted with ethyl acetate. The combined organic phase was dried, concentrated to give 2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline. The product was used in the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 321.1.

Aufarbeitung

  1. additionAfter addition
  2. temperatureat reflux under Nitrogen for 3 h
  3. filtrationfiltered through a pad of celite
  4. customThe solvent of ethanol in filtrate was removed under reduced pressure
  5. extractionthe water phase was extracted with ethyl acetate
  6. customThe combined organic phase was dried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8ad61d17f5d042288f6a29ed579881dd
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546427B2

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