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

HRID 540313노트

반응식

HRID 540313 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d9b8a6da341d4f32b0b0fa5cc33e4655
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

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