Water → 6-[2-Nitro-4-(trifluoromethyl)phenoxy]quinoline-2-carbonitrile

HRID 446193

반응식

HRID 446193 반응식
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:13])[CH:9]=2)[N:4]=1)#[N:2].[Cl-].[N+:15]([C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(Cl)Cl>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][C:19]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:25])[F:26])=[CH:23][C:18]=3[N+:15]([O-:17])=[O:16])[CH:9]=2)[N:4]=1)#[N:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 144295346-Hydroxyquinoline-2-carbonitrileHCID 666082642-Nitro-4-trifluoromethylbenzene chloride

생성물 1

HCID 587976996-[2-Nitro-4-(trifluoromethyl)phenoxy]quinoline-2-carbonitrile수율 35%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

The mixture of 2-cyano-6-hydroxyquinoline (0.50 g, 2.94 mmol), 2-nitro-4-trifluoromethylbenzene chloride (0.67 g, 2.94 mmol) and potassium carbonate (0.41 g, 2.97 mmol) in 30 ml of DMSO was heated to 100° C. for 30 min. Upon cooling to room temperature, the mixture was poured into 30 ml of cold water and exacted three times with methylene chloride. The combined organic layer was washed with water and dried over magnesium sulfate. The product was purified by flash chromatography using heptane/methylene chloride (1:2) as eluent in a yield of 35%.

후처리

  1. temperatureUpon cooling to room temperature
  2. washThe combined organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-72f8c18f7b4848229b893b2263e6f56f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476450B2

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