Methyl iodide → 1,7-Dimethyl-1H-indole

HRID 1362034

반응식

HRID 1362034 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.[CH3:13]I.[NH4+].[Cl-]>CN(C=O)C>[CH3:13][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:3])[CH:9]=[CH:10]1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 702757-Methylindole

생성물 1

HCID 5893901,7-Dimethyl-1H-indole수율 103.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (1.15 g, 28.7 mmol, 60% in mineral oil) was rinsed with hexanes and then suspended in DMF (20 mL). To this suspension was added 7-methylindole (2.5 g, 19 mmol) portionwise. Gas evolution was allowed to subside between additions. The resulting brown mixture was stirred at room temperature for 15 min and then CH3I (2.71 g, 95.5 mmol) was added in one portion. The exothermic reaction was cooled to 30° C. and stirred for 1 h. Saturated aqueous NH4Cl (10 mL) was added and the mixture was concentrated under reduced pressure. The residue was combined with water (100 mL) and the mixture was then extracted with diethyl ether (3×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (2.85 g, quantitative) as a red-pink oil which crystallized upon vacuum drying: 1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=7.6 Hz, 1H), 6.97-6.87 (m, 3H), 6.41 (d, J=3.1 Hz, 1H), 4.04 (s, 3H), 2.7 (s, 3H).

후처리

  1. customThe exothermic reaction
  2. temperaturewas cooled to 30° C.
  3. stirringstirred for 1 h
  4. concentrationthe mixture was concentrated under reduced pressure
  5. extractionthe mixture was then extracted with diethyl ether (3×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-767b1d7b253f4cdca670e0645d544f68
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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