Glycerol → 7-(Trifluoromethyl)quinoline

HRID 1808329

反応式

HRID 1808329 の反応式
S(=O)(=O)(O)O.[F:6][C:7]([F:16])([F:15])[C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].O[CH2:18][CH:19]([CH2:21]O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.II>[F:6][C:7]([F:15])([F:16])[C:8]1[CH:9]=[C:10]2[C:12]([CH:18]=[CH:19][CH:21]=[N:11]2)=[CH:13][CH:14]=1

参加物

7

反応物 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 73753-(Trifluoromethyl)anilineHCID 10340Sodium Carbonate

生成物 1

HCID 4596147-(Trifluoromethyl)quinoline収率 22.13%

試薬・触媒・溶媒 2

HCID 807Iodine触媒HCID 962Water溶媒

反応条件

温度
165 °C

実験手順

Conc. sulfuric acid (4.56 g; 1.5 equiv.) was added dropwise to a mixture of 3-(trifluoromethyl)aniline (5 g; 1 equiv.), glycerol (5.14 g; 1.8 equiv.) and iodine (150 mg). The resulting reaction mixture was stirred for 1 hour at 80-90° C. and for 3 hours at 160-170° C. When the conversion was complete, the reaction mixture was diluted at room temperature with 100 ml of water, neutralised with sodium carbonate and extracted 4× with 200 ml of dichloromethane. The combined organic phases were dried over sodium sulfate, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, 10% EtOAc/hexane). 7-(Trifluoromethyl)quinoline (1.35 g; 22.13%) was obtained in the form of a white crystalline solid.

後処理

  1. customThe resulting reaction mixture
  2. extractionextracted 4× with 200 ml of dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography (silica gel, 10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-1d27ae53d74e492db446c5b28b6471dd
出典データセット
uspto-grants-2013_01
特許番号
US08357717B2

関連ノート

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