Sodium Hydroxide → 5-Chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amine

HRID 540313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 540313
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]=[C:11]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14]2)[CH3:12])[C:3]=1[C:4]#[N:5].CN(C)C(=O)C.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:3]=1[C:4]([NH2:5])=[CH:12][C:11]([N:13]1[CH2:19][CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14]1)=[N:10]2

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 712545892-Chloro-6-{[1-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)ethylidene]amino}benzonitrile

Produkt 1

HCID 712553505-Chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amineAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

The mixture of 2-chloro-6-{[1-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)ethylidene]amino}benzonitrile (6 g, 18.5 mmol), zinc chloride (2.52 g, 18.5 mmol) and N,N-dimethyl-acetamide (18 mL) was heated with stirring at 160° C. for 3 hours under argon. After the reaction was allowed to cool to about 40° C., sodium hydroxide (2 N, 20 mL) was added and then stirred for 10 minutes at room temperature. The reaction mixture was poured into water and the solid was collected by filtration, washed with water and dried in vacuo to give 5 g of product as an off-white powder (yield was 83.3%). MS obsd. (ESI+) [(M+H)+] 324.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto cool to about 40° C.
  3. stirringstirred for 10 minutes at room temperature
  4. filtrationthe solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d9b8a6da341d4f32b0b0fa5cc33e4655
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871756B2

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