Hydrochloric Acid → 6-Chloro-4-(trifluoromethyl)pyridine-2-carboxylic acid

HRID 19805ノート

反応式

HRID 19805 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[Mn]([O-])(=O)(=O)=[O:14].C([N+](CCCC)(CCCC)CCCC)CCC.OS([O-])=O.[Na+].[ClH:40].[OH2:41]>N1C=CC=CC=1>[Cl:40][C:2]1[N:3]=[C:4]([C:12]([OH:14])=[O:41])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 27366262-Chloro-6-methyl-4-(trifluoromethyl)pyridineHCID 11760202Tetrabutylammonium permanganateHCID 23665763Sodium Bisulfite

生成物 1

HCID 210859856-Chloro-4-(trifluoromethyl)pyridine-2-carboxylic acid収率 67%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 300 mg of 2-chloro-6-methyl-4-(trifluoromethyl)-pyridine (1.49 mmol) in pyridine (5 ml) was added a solution of 1.61 g of tetrabutylammonium permanganate (4.46 mmol) in pyridine (4.5 ml) and the reaction mixture was stirred at 80° C. for 3 h. The reaction mixture was then poured into a mixture of water and ice and then NaHSO3 solution (40% in water) was added until the color turned light yellow. The mixture was then acidified by addition of 2N HCl and extracted with ethyl acetate. The combined organic layers were then washed with 1N HCl and brine, dried (Na2SO4), filtered and concentrated. The remaining residue was purified by chromatography (DCM/MeOH 100:0 to 90:10) to yield 224 mg (67%) of a gray liquid. MS (ISP) 224.3 (M−H)−.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were then washed with 1N HCl and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe remaining residue was purified by chromatography (DCM/MeOH 100:0 to 90:10)

出典と根拠

ORDレコード
ord-ad385a6737f54efebaab70ef0ab45955
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

反応ノート

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