Hydrochloric Acid → 1-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

HRID 862208노트

반응식

HRID 862208 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.C([O:25][N:26]=O)(C)(C)C.Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8](=[N:26][OH:25])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 119771402-(2-Fluoropyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]ethanone

생성물 1

HCID 1363810621-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of 2-(2-fluoropyridin-4-yl)-1-(3-trifluoromethylphenyl)ethanone (10.80 g, 0.038 mole) in ethanol (200 mL), at -10° C., under argon, was added tert-butylnitrite (5.0 mL, 0.042 mol) followed by hydrogen chloride (12.2 mL, 2.5M in ethanol, 0.031 mole) dropwise while maintaining the temperature below -5° C. Upon completion of addition, the reaction was allowed to warm to room temperature for 2 hours. The reaction was concentrated in vacuo, diluted with water (100 mL), basified with saturated sodium bicarbonate (200ml). This mixture was then extracted with ethyl acetate (1×600 mL, 2×300 mL). The organic layers were combined, washed with water (300 mL), washed with brine (300 mL), dried over anhydrous sodium sulfate, filtered and concentrated to an oil (11.4 g).

후처리

  1. temperaturewhile maintaining the temperature below -5° C
  2. additionUpon completion of addition
  3. concentrationThe reaction was concentrated in vacuo
  4. additiondiluted with water (100 mL)
  5. extractionThis mixture was then extracted with ethyl acetate (1×600 mL, 2×300 mL)
  6. washwashed with water (300 mL)
  7. washwashed with brine (300 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil (11.4 g)

출처 및 근거

ORD 기록
ord-6abde5afbf754b80b3a5c907489def6a
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05717100

반응 노트

불러오는 중…