Nitromethane → 1-[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol

HRID 623318노트

반응식

HRID 623318 반응식
[Cl:1][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[Na+].[N+:16]([CH3:19])([O-:18])=[O:17]>>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[CH2:19][N+:16]([O-:18])=[O:17])=[CH:6][CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[N:9]=1

참가 물질

4

반응물 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 467399062-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde

생성물 1

HCID 867325451-[2-Chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol수율 72%

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) (70 g, 1.0 eq.) in nitro methane (700 mL) was added sodium hydroxide (6.7 g, 0.5 eq.) at room temperature. The resulting reaction mixture was heated to 100° C. and stirred for 2 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under reduced pressure to remove nitro methane quenched with ice water (500 mL) and extracted with ethyl acetate (2×1.0 L). The combined organic layer was washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get pure 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (65.0 g, 72.0%).

후처리

  1. customThe resulting reaction mixture
  2. customAfter completion of reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customto remove nitro methane
  5. customquenched with ice water (500 mL)
  6. extractionextracted with ethyl acetate (2×1.0 L)
  7. washThe combined organic layer was washed with water (500 mL), brine (500 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fd095199b01843ab9f17da757d74d52c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301526B2

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