6-chloro-1H-indole-5-carbonitrile → HCID 82408684, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]#[N:12]>CO.N.[Ni]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[CH2:11][NH2:12]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 242 (43 mg, 0.24 mmol) in MeOH (10 mL) and 7M NH3 in MeOH (5 mL) was added Raney nickel and the reaction mixture was stirred vigorously under hydrogen (1 atm.) at RT for 3 h. The reaction mixture was filtered through a pad of Celite® and concentrated under reduced pressure to afford (6-chloro-1H-indol-5-yl)methanamine (244) as pale oil: MS (ESI)=164.1 [M−NH2]+.
Workup
- filtrationThe reaction mixture was filtered through a pad of Celite®
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-92e38107ab864bb88001239756bb8c64
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637537B2
Reaction notes
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