Sodium Hydroxide → 6-amino-1H-indole-7-carboxylic acid

HRID 245604Notes

Reaction equation

HRID 245604 reaction equation
C[O:2][C:3]([C:5]1[C:6]([NH2:14])=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)=[O:4].[OH-].[Na+]>O1CCOCC1.CO>[NH2:14][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57990185methyl 6-amino-1H-indole-7-carboxylate

Product 1

HCID 223138806-amino-1H-indole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 85.2 mg (0.45 mmol) of 6-amino-1H-indole-7-carboxylic acid methyl ester in 4 mL of dioxane and 1 mL of methanol, is added 0.45 mL (0.9 mmol) of an aqueous solution of NaOH 2N. The mixture is stirred over the night at 60° C. A new addition of 0.22 mL (0.45 mmol) of an aqueous solution of NaOH 2N is made and the mixture is stirred again 6 h at 60° C. and then cooled to ambient temperature. After evaporation of all the solvents, a crude yellowish residue is obtained and used directly in the next step; 1H-NMR (MeOD4, 400 MHz): 7.51 (m, 1H), 7.05 (d, 1H), 6.55 (d, 1H), 6.33 (m, 1H) ppm.

Workup

  1. stirringthe mixture is stirred again 6 h at 60° C.
  2. temperaturecooled to ambient temperature
  3. customAfter evaporation of all the solvents
  4. customa crude yellowish residue is obtained

Sources & evidence

ORD record
ord-f120545c63e744f48ed16a60086fe2ca
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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