Dimethylformamide → 2-Chloro-4-(trifluoromethyl)quinoline

HRID 513732ノート

反応式

HRID 513732 の反応式
CN(C=O)C.[F:6][C:7]([F:20])([F:19])[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=O)[CH:9]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:10]1[CH:9]=[C:8]([C:7]([F:20])([F:19])[F:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 27593472-Hydroxy-4-(trifluoromethyl)quinoline

生成物 1

HCID 27829122-Chloro-4-(trifluoromethyl)quinoline収率 29%

反応条件

温度
90 °C

実験手順

DMF (cat.) was added to a solution of 4-trifluoromethyl-1H-quinolin-2-one 465 (160 mg, 0.75 mmol) in POCl3 (2 ml) and the mixture was heated at 90° C. for 1 h. After cooling, the mixture was concentrated in vacuo and the residue was poured into an ice cold solution of NaHCO3 solution. The aqueous phase was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (50 mg, 29%) which was used in the next step without further purification.

後処理

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. additionthe residue was poured into an ice cold solution of NaHCO3 solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-79f1f1d9d02242dda64edece07364eac
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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