Ammonium Hydroxide → 1H-Indole-5-carboxamide

HRID 440923Notes

Reaction equation

HRID 440923 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N1C=CN=C1)([N:15]1C=CN=C1)=O.[OH-].[NH4+]>CN(C)C=O>[CH:7]1[C:6]([C:10]([NH2:15])=[O:12])=[CH:5][C:4]2[CH:3]=[CH:2][NH:1][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 742801H-Indole-5-Carboxylic Acid

Product 1

HCID 149732201H-Indole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.06 gm (50 mMol) indole-5-carboxylic acid in 150 mL dimethylformamide were added 8.11 gm (50 mMol) carbonyldiimidazole and the reaction mixture stirred at ambient temperature for 3 hours. The reaction mixture was then added dropwise to 150 mL concentrated ammonium hydroxide and the reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure to give a viscous oil which was subjected to silica gel chromatograpy, eluting with a gradient of dichloromethane containing 0-10% methanol. Fractions shown to contain product were combined and concentrated under reduced pressure to give the title compound as an oil which crystallizes upon standing. 1H-NMR (CDCl3): δ8.18 (s, 1H); 7.74 (d, 1H); 7.45 (d, 1H); 7.35 (s, 1H); 6.65 (s, 1H).

Workup

  1. stirringthe reaction mixture was stirred for 18 hours at ambient temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a viscous oil which
  4. washeluting with a gradient of dichloromethane containing 0-10% methanol
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b11fef0f0ccc4746bdf421c2158ab1a5
Source dataset
uspto-grants-1996_05
Patent number
US05521196

Reaction notes

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