Sodium Hydroxide → (1H-indol-4-yl)methanamine

HRID 393006

반응식

HRID 393006 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]#[N:17])[C:10]=2[CH:9]=[CH:8]1.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:16][NH2:17])[C:10]=2[CH:9]=[CH:8]1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 38176024-CyanoindoleHCID 21226445Aluminium lithium hydride

생성물 1

HCID 280302(1H-indol-4-yl)methanamine수율 80.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium aluminum hydride (3.80 g, 100.0 mmol) was added in 0.5 g portions over 30 min to a solution of 1H-indole-4-carbonitrile (prepared according to Clark, Robin D.; Repke, David B. J. Heterocycl. Chem. 1985, 22, 121-5; 7.50 g, 52.8 mmol) in tetrahydrofuran (250 mL). The mixture was heated at reflux for 30 min. A solution of 1 M sodium hydroxide was added to quench excess lithium aluminum hydride. The mixture was filtered and the filter cake was washed with water. The filtrate was first made acidic with 1 N HCl and then made basic again by the addition of saturated aqueous NaHCO3. The water layer was then extracted with nBuOH. Evaporation of nBuOH, and drying under vacuum gave 1H-indole-4-methanamine (6.24 g, 80%) as a beige solid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 min
  3. customto quench excess lithium aluminum hydride
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with water
  6. additionmade basic again by the addition of saturated aqueous NaHCO3
  7. extractionThe water layer was then extracted with nBuOH
  8. customEvaporation of nBuOH
  9. customdrying under vacuum

출처 및 근거

ORD 기록
ord-d91ce68bf8464e15b7cf6436b971fcec
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803384B2

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