HCID 11321809, compound → 3H-Benz[e]indole

HRID 890591Notes

Reaction equation

HRID 890591 reaction equation
[H][H].[N+]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]#[N:18])([O-])=O>C(O)C.C(O)(=O)C.[Pd]>[CH:16]1[C:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH:14]=[CH:15][C:6]=2[NH:18][CH:17]=1

Participants

6

Reactant 2

HCID 11321809HCID 11321809, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 113442113H-Benz[e]indole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

At ambient temperature and under 4 bars of hydrogen, hydrogenate 33 g of (2-nitro-1-naphthyl)acetonitrile (0.155 mol) dissolved in 630 ml of ethanol containing 10% water and 6.3 ml of pure acetic acid, using 19 g of 10% palladium-on-carbon. After absorption has ceased, filter off the catalyst, concentrate the solvent in vacuo and then take up the residue in 250 ml of dichloromethane; wash the organic phase with 100 ml of 0.1N potassium hydroxide solution and then dry the organic phase over magnesium sulphate, filter and concentrate.

Workup

  1. customAfter absorption
  2. filtrationfilter off the catalyst
  3. concentrationconcentrate the solvent in vacuo
  4. washwash the organic phase with 100 ml of 0.1N potassium hydroxide solution
  5. dry with materialdry the organic phase over magnesium sulphate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-8ac5494928d146288a367fe5ca9a968b
Source dataset
uspto-grants-2006_02
Patent number
US06998403B2

Reaction notes

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