Water → 46054-15-3

HRID 983946

Reaction equation

HRID 983946 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([CH2:5][CH2:4][NH2:1])[CH:14]=2)[CH:10]=[CH:11]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 697441266-(2-Nitrovinyl)-1H-indole

Product 1

HCID 1722110046054-15-3Yield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(2-Nitrovinyl)-1H-indole (1.0 g) in tetrahydrofuran (100 mL) was added portionwise lithium aluminum hydride (0.95 g) and the resulting mixture stirred at reflux for 1 hour. The reaction mixture was treated sequentially with water (0.95 mL), 15% sodium hydroxide (0.95 mL), and water (2.85 mL). The resulting suspension was filtered and the filtrate diluted with ethyl acetate (200 mL), washed with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride, dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide 0.525 g (62%) of the desired compound.

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationThe resulting suspension was filtered
  3. additionthe filtrate diluted with ethyl acetate (200 mL)
  4. washwashed with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc1989c0485c40858ba5b7c0d6a86690
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Linked notes

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