2-(1H-Pyrrolo[3,2-c]pyridin-3-yl)acetonitrile → 2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine

HRID 1593506Notes

Reaction equation

HRID 1593506 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1.[H][H]>C(O)C.[NH4+].[OH-].[Rh]>[NH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[N:6][CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 2

HCID 226630522-(1H-Pyrrolo[3,2-c]pyridin-3-yl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 226629862-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of (1H-pyrrolo[3,2-c]pyridin-3-yl)-acetonitrile (0.260 g, 1.66 mmol) and 5% rhodium on alumina (0.26 g) in ethanol (10 mL) and concentrated NH4OH (5 mL) is placed under 55 psi hydrogen pressure on a Parr shaker. After 24 h at ambient temperature, the reaction mixture is filtered through Celite and concentrated in vacuo to afford the title amine, identified by NMR and mass spectral analyses.

Workup

  1. filtrationthe reaction mixture is filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4e89e60ac03425587cef80e3affc944
Source dataset
uspto-grants-2007_11
Patent number
US07297705B2

Reaction notes

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