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

HRID 401261ノート

反応式

HRID 401261 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-23e48eb5d37940e08021d695c0e996e5
出典データセット
uspto-grants-2014_06
特許番号
US08741925B2

反応ノート

読み込み中…