Hydrochloric Acid → 1-(2-Methoxy-3-nitrophenyl)ethanone

HRID 629188노트

반응식

HRID 629188 반응식
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[C:14](=O)([O-])[O-].[K+].[K+].IC.Cl>CN(C=O)C>[CH3:14][O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2회HCID 11430Potassium CarbonateHCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

생성물 1

HCID 155794711-(2-Methoxy-3-nitrophenyl)ethanone수율 97.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A slurry of 1-(2-hydroxy-3-nitrophenyl)ethanone (1.00 g, 5.52 mmol) and potassium carbonate (3.05 g, 22.08 mmol) in DMF (20 mL) was stirred at room temperature for 30 minutes, then iodomethane (1.338 mL, 16.56 mmol) was added dropwise and the resulting mixture was allowed to stir at room temperature overnight. LCMS indicated some un-reacted starting material remained, therefore additional iodomethane (1.338 mL, 16.56 mmol) was added and the mixture was warmed to 50° C. over 2 days. Reaction was quenched by the addition of water to give a solution followed by adjusting the pH with 1N HCl to ˜7. The resulting solution was extracted with ethyl acetate (80 mL×3) and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the product, 1-(2-methoxy-3-nitrophenyl)ethanone (1.05 g, 5.38 mmol, 97% yield) as a tan oil. HPLC (Method N) RT=1.86 minutes.

후처리

  1. temperaturethe mixture was warmed to 50° C. over 2 days
  2. customReaction
  3. customwas quenched by the addition of water
  4. customto give a solution
  5. extractionThe resulting solution was extracted with ethyl acetate (80 mL×3)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a8dc8e1cda124ce4bd4d084332cec486
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315494B2

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