Dimethylformamide → 3-Chloroquinoline-7-carbonitrile

HRID 1465739노트

반응식

HRID 1465739 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([Cl:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14].CN(C=O)C>C(Cl)Cl>[Cl:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:13]#[N:14])[CH:11]=2

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 533932407-Bromo-3-chloroquinolineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 895252713-Chloroquinoline-7-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
150 °C

실험 절차

To a flask containing a stir bar was added 7-Bromo-3-chloroquinoline (1.0 g, 4.1 mmol), CuCN (0.55 g, 6.2 mmol), and DMF (25 mL). The mixture was then refluxed at 150° C. overnight. When the reaction was complete, as evidenced by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered off. The crude product was adsorbed onto silica gel and purified by silica gel column chromatography (Hexanes:DCM→1:1) to provide the title product.

후처리

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to room temperature
  3. filtrationwhich was filtered off
  4. custompurified by silica gel column chromatography (Hexanes:DCM→1:1)

출처 및 근거

ORD 기록
ord-4e4be921e4394c1eb71db861ed04959f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999991B2

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