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

HRID 19805노트

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HRID 19805 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매2회

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온도
80 °C

실험 절차

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)−.

후처리

  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)

출처 및 근거

ORD 기록
ord-ad385a6737f54efebaab70ef0ab45955
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745477B2

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