Ammonium Hydroxide → 1H-Indole-2-carboxamide

HRID 1866228Notes

Reaction equation

HRID 1866228 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)([N:15]1C=CN=C1)=O.[NH4+].[OH-]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH2:15])=[O:12]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acid

Product 1

HCID 5948321H-Indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add to the 2-indole carboxylic acid (31.0 mmol) dissolved in anhydrous THF (50 ml), carbonyldiimidazole (1.10 equiv, 5.5 g, 34.0 mmol) and stir 1 h. Then add concentrated NH4OH (50 mL) in one portion and stir the reaction at rt. After 16 hours collect the solid that separates by filtration, wash with H2O and dry under vacuum at 40° C. to afford the desired 2-indole carboxamide.

Workup

  1. customthe reaction at rt
  2. customAfter 16 hours collect the solid that separates
  3. filtrationby filtration
  4. washwash with H2O
  5. customdry under vacuum at 40° C.

Sources & evidence

ORD record
ord-4656ffe16d324ffd9737f6a59f787293
Source dataset
uspto-grants-2009_12
Patent number
US07629376B2

Reaction notes

Loading…