Ammonia → (1-tosyl-1H-indol-6-yl)methanamine

HRID 475179Notes

Reaction equation

HRID 475179 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].N>CO.[Ni]>[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][NH2:21])[CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 712719531-tosyl-1H-indole-6-carbonitrile

Product 1

HCID 71272360(1-tosyl-1H-indol-6-yl)methanamineYield 78.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 34 (100 mg, 0.34 mmol) and 7 M ammonia solution in MeOH (5 mL) was added Raney Ni (10 mg) and the mixture was stirred vigorously under H2 (1 atm.) atmosphere at RT for 18 h. The catalyst was filtered was and the filtrate concentrated in vacuo to afford 80 mg (78%) of (1-tosyl-1H-indol-6-yl)methanamine (36) as syrup: MS (ESI) m/z=301.2 [M+1]+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-175b88fac8654803b4cb87256bbb77cb
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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