HCID 74890582, compound → HCID 82408684, compound

HRID 475274Notes

Reaction equation

HRID 475274 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

HCID 74890582HCID 74890582, compound

Product 1

HCID 82408684HCID 82408684, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent2×

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

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. 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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