Dimethyl Sulfate → 1,3-Dihydro-5-methoxy-1-methyl-2H-indol-2-one

HRID 1410349노트

반응식

HRID 1410349 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2.[CH3:15]OS(OC)(=O)=O>C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:15])[C:9](=[O:14])[CH2:8]2

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 15142865-Methoxyoxindole

생성물 1

HCID 91021941,3-Dihydro-5-methoxy-1-methyl-2H-indol-2-one수율 53.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A dry round-bottom flask was charged with NaH (60% wt) (64 mg, 1.61 mmol) and toluene (2.0 mL). The suspension was heated to 100° C. and then 5-methoxyindolin-2-one (250 mg, 1.53 mmol) was added. After 30 min at 100° C. Me2SO4 (0.16 mL, 1.68 mmol) was added and the temperature maintained at 100° C. for 2.5 h. The reaction was cooled to room temperature and the solvent removed. The residue was purified by column chromatography (silica gel, 25-33% EtOAc in hexane) to give 5-methoxy-1-methylindolin-2-one (beige solid, 144 mg, 53%); MS ESI 164.1 [M+H]+, calcd for [C9H9NO2+H]+ 164.07.

후처리

  1. temperaturethe temperature maintained at 100° C. for 2.5 h
  2. temperatureThe reaction was cooled to room temperature
  3. customthe solvent removed
  4. customThe residue was purified by column chromatography (silica gel, 25-33% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-860679f21e074b1bbd4dffe93a2f1652
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921545B2

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