2-(1H-Pyrrolo[3,2-c]pyridin-3-yl)acetonitrile → 2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine
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]=1Participants
6
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
- filtrationthe reaction mixture is filtered through Celite
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-27f0c758ece04136bd6ca923768979fe
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585876B2
Reaction notes
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