Dimethylcarbamoyl Chloride → 7-Chloro-4-phenylquinoline-2-carbonitrile

HRID 2422566노트

반응식

HRID 2422566 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:29][N:30](C)C(Cl)=O.C[Si](C#N)(C)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][C:8]([C:29]#[N:30])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 6598Dimethylcarbamoyl ChlorideHCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 113454577-Chloro-4-phenylquinoline

생성물 1

HCID 597749247-Chloro-4-phenylquinoline-2-carbonitrile

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of 7-chloro-4-phenylquinoline (Example 39, Step 1) (3.0 g, 12.5 mmol) and m-CPBA (2.6 g, 15.0 mmol) in chloroform (50 mL) was stirred at room temperature for 3 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted twice with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was dissolved in chloroform (50 mL). N,N-Dimethylcarbamoyl chloride (2.4 mL, 25.0 mmol) and trimethylsilyl cyanide (3.4 mL, 25.0 mmol) were added to this solution and stirred at room temperature for 2 days. Saturated aqueous NaHCO3 solution was added and the mixture stirred for 30 min. The organic layer was removed, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was used in the next step without further purification.

후처리

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution
  2. extractionextracted twice with dichloromethane
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe resulting crude product was dissolved in chloroform (50 mL)
  7. stirringthe mixture stirred for 30 min
  8. customThe organic layer was removed
  9. extractionthe aqueous layer was extracted with dichloromethane
  10. washThe combined organic layers were washed with water, brine
  11. dry with materialdried over anhydrous MgSO4
  12. customThe solvent was removed under reduced pressure
  13. customthe resulting crude product was used in the next step without further purification

출처 및 근거

ORD 기록
ord-60945e4edb9042d7a5695b62c3f32159
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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