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

HRID 540313Notes

Reaction equation

HRID 540313 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 712553505-Chloro-2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amineYield 83.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9b8a6da341d4f32b0b0fa5cc33e4655
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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