Methyl iodide → 8-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1811394노트

반응식

HRID 1811394 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[H-].[Na+].[H][H].[CH3:18]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH3:18])[C:10](=[O:13])[CH2:9][CH2:8]2

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 133754763,4-Dihydro-8-methoxy-2(1H)-quinolinoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 133841968-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

8-Methoxy-3,4-dihydro-1H-quinolin-2-one (15 g) was dissolved in DMF (150 ml), and 3.6 g of sodium hydride (60% in oil) was added under ice cooling. After the addition, stirring was carried out at room temperature until the generation of hydrogen stopped. The resulting mixture was cooled with ice water again, and 5.8 ml of methyl iodide was added dropwise, followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to thereby obtain 16.7 g (yield: 96%) of 8-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one.

후처리

  1. additionAfter the addition
  2. stirringby stirring at room temperature overnight
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-96f527c4a0e8489b880b21cbe161553e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362252B2

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