Methyl iodide → 1-methyl-1H-indole-5-carbaldehyde

HRID 1362045

반응식

HRID 1362045 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].CI.[C:16](OCC)(=O)C>CN(C=O)C>[CH3:16][N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 589040Indole-5-carboxaldehyde

생성물 1

HCID 75375341-methyl-1H-indole-5-carbaldehyde수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of indole-5-carbaldehyde (1.0 g, 6.9 mmol) in DMF (15 mL) was added sodium hydride (303 mg of 60% dispersion in oil, 7.59 mmol) in 3 portions. The mixture was stirred for 30 mins. Methyl iodide (1.96 g, 13.8 mmol) was then added and the mixture was stirred overnight. Ethyl acetate (200 mL) was added and solution was washed with H2O (3×20 mL) and brine (25 mL) dried over MgSO4 and concentrated to afford N-methylindole-5-carboxaldehyde as an orange oil (1.0 g, 91%). 1H NMR (200 MHz, CDCl3) δ 10.05 (s, 1H), 8.09 (s, 1H), 7.90-7.80 (m, 1H), 7.35-7.15 (m, 2H), 6.85-6.80 (m, 1H), 3.95 (s, 3H).

후처리

  1. stirringthe mixture was stirred overnight
  2. washsolution was washed with H2O (3×20 mL) and brine (25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1e58c4510edc411f9995ba647d2f4e31
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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