Dimethylformamide → Quinoline-6-carbonyl chloride

HRID 70804

반응식

HRID 70804 반응식
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CN(C)C=O.C(Cl)(=O)C([Cl:22])=O>ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([Cl:22])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 825716-Quinolinecarboxylic acid

생성물 1

HCID 12391963Quinoline-6-carbonyl chloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Quinoline-6-carboxylic acid (1.0 g) was dissolved in dichloromethane. N,N-dimethylformamide (300 μL) and oxalyl chloride (1.2 g) were added to this solution at room temperature and stirred for two hours followed by reflux for 20 minutes. The solvent was removed under the reduced pressure, and quinoline-6-carbonyl chloride was obtained as a crude product, which was then dissolved in dichloromethane. To this solution, 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylaniline (1.6 g) dissolved in dichloromethane and pyridine (1.2 g) were added and stirred at room temperature for 5 hours. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined and washed with 1N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,6-dimethylphenyl]quinoline-6-carboxamide (2.0 g, yield 78%).

후처리

  1. temperatureby reflux for 20 minutes
  2. customThe solvent was removed under the reduced pressure

출처 및 근거

ORD 기록
ord-dba1667abba644e8b8d54b6cdde1ef30
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822691B2

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