HCID 67291098, Verbindung → HCID 67291611, Verbindung

HRID 1036932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036932
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[CH2:3]1>[Cl-].[NH4+].C(O)C.[Fe]>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[CH2:3]1

Komponenten

5

Edukt 1

HCID 67291098HCID 67291098, Verbindung

Produkt 1

HCID 67291611HCID 67291611, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a suspension of 4,4,6-trimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (12.3 g, 40 mmol) in saturated aqueous ammonium chloride and ethanol (100 mL) was added powder iron (9.3 g, 160 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-(4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (9.7 g). The product was used in the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 267.1.

Aufarbeitung

  1. additionAfter addition
  2. temperatureat reflux under nitrogen for 3 h
  3. filtrationand filtered 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-6ed4a23f7ebd4e498feb274e26b726ab
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546427B2

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