Dimethylformamide → 4-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

HRID 1935030노트

반응식

HRID 1935030 반응식
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[C:9]([C:14]#[N:15])=[CH:10][NH:11]2)=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2].C(Cl)(=O)C([Cl:22])=O.CN(C=O)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].C(Cl)Cl>[Cl:22][C:8]1[C:7]2[C:12](=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([O:17][CH3:18])[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:14]#[N:15]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 65578Oxalyl chlorideHCID 104904723-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-

생성물 1

HCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile수율 89.1%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

Mixed 122 mg (0.50 mmol) 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarbonitrile and 2.0 ml methylene chloride under N2 and kept temperature near 25° C. Added 218 μl (2.5 mmol) oxalyl chloride and 10 μl (0.125 mmol) DMF. Stirred overnight, diluted with chloroform and stirred in saturated sodium bicarbonate until basic. Separated layers and dried organics with magnesium sulfate, stripped solvent and dried in vacuo, giving 117 mg of tan solid: mass spectrum (electrospray m/e): M+H=262.8, 264.8.

후처리

  1. customnear 25° C
  2. customdried in vacuo

출처 및 근거

ORD 기록
ord-d1c9290b9ee34a7bb5392bdb1686107f
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384051B1

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