Ammonium Hydroxide → 1H-Indole-2-carboxamide

HRID 1677801Notes

Reaction equation

HRID 1677801 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 a solution of indole-2-carboxylic acid 3 (31.0 mmol) and anhydrous THF (50 ml), carbonyldiimidazole (1.10 equiv., 5.5 g, 34.0 mmol). Stir for 1 h and add conc. NH4OH (50 mL) in one portion to the thick suspension. Stir at rt and after 16 h collect the solid by filtration, wash with H2O and dry in vacuuo at 40° C. to afford the indole-2-carboxamide 4 (R2═R3═H).

Workup

  1. stirringStir at rt and after 16 h
  2. customcollect the solid
  3. filtrationby filtration
  4. washwash with H2O
  5. customdry in vacuuo at 40° C.

Sources & evidence

ORD record
ord-6db4fe67d8074e1bb11d031b3d74a7f8
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

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