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

HRID 446193

反応式

HRID 446193 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-72f8c18f7b4848229b893b2263e6f56f
出典データセット
uspto-grants-2013_07
特許番号
US08476450B2

関連ノート

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