Dimethylformamide → 1h-Indole-3-acetonitrile, 6-nitro-

HRID 423754노트

반응식

HRID 423754 반응식
[CH3:1][N:2](C=O)C.CI.CN(C)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[C-]#N.[K+]>O.C1COCC1>[N+:20]([C:16]1[CH:15]=[C:14]2[C:19]([C:11]([CH2:10][C:1]#[N:2])=[CH:12][NH:13]2)=[CH:18][CH:17]=1)([O-:22])=[O:21]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 233856-Nitrogramine

생성물 1

HCID 2523851h-Indole-3-acetonitrile, 6-nitro-수율 36%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of DMF (35 mL) and MeI (74.6 g, 0.53 mol) in water (35 mL) and THF (400 mL) was added dimethyl-(6-nitro-1H-indol-3-ylmethyl)-amine (23 g, 0.105 mol). After the reaction mixture was refluxed for 10 min, potassium cyanide (54.6 g, 0.84 mol) was added and the mixture was kept refluxing overnight. The mixture was then cooled to room temperature and filtered. The filtrate was washed with brine (300 mL×3), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give (6-nitro-1H-indol-3-yl)-acetonitrile (B-9-a) (7.5 g, 36%).

후처리

  1. temperatureAfter the reaction mixture was refluxed for 10 min
  2. temperaturethe mixture was kept refluxing overnight
  3. filtrationfiltered
  4. washThe filtrate was washed with brine (300 mL×3)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-18e4f848d6734ac9ba8134c0a65c9709
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101767B2

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