2-(7-Cyano-1H-indol-1-yl)acetic acid → 2-(7-(Aminomethyl)-1H-indol-1-yl)acetic acid

HRID 453917Notes

Reaction equation

HRID 453917 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:8]2)#[N:2].[H][H]>CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:8]2

Participants

5

Reactant 2

HCID 594737242-(7-Cyano-1H-indol-1-yl)acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 594736972-(7-(Aminomethyl)-1H-indol-1-yl)acetic acidYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney Ni (7.0 g) was added to a solution of 2-(7-cyano-1H-indol-1-yl)acetic acid (700 mg, 3.5 mmol) in MeOH (15 ml), and the mixture was hydrogenated for 6 h at RT and 60 psi hydrogen in a Parr apparatus. The reaction mixture was filtered over celite and the filtrate was concentrated under vacuum. The crude product so obtained was used directly in the following stage without being purified further. Yield: 96% (692 mg, 3.36 mmol)

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8fff7e95da214424820948a9ade5d236
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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