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

HRID 552044ノート

反応式

HRID 552044 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-66f723c70bac4a4cbec8a9885b6d9ae4
出典データセット
uspto-grants-2011_05
特許番号
US07951550B2

反応ノート

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