Ammonium Hydroxide → 1H-Indole-5-carboxamide

HRID 863467Notes

Reaction equation

HRID 863467 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.

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-9349a567414f45f8819bdaf25f4aa36c
Source dataset
uspto-grants-1998_02
Patent number
US05721252

Reaction notes

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