Sodium Hydroxide → HCID 43316595, compound

HRID 2281644Notes

Reaction equation

HRID 2281644 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][C:15](=[O:21])[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].[OH-].[Na+]>CO>[CH2:19]([N:16]([CH2:17][CH3:18])[C:15]([CH2:14][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=2[CH:7]=[CH:8]1)=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67086835HCID 67086835, compound

Product 1

HCID 43316595HCID 43316595, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Diethylcarbamoylmethyl-1H-indole-4-carboxylic acid methyl ester (480 mg, 1.665 mmol) in MeOH (5 ml) is added 2 M NaOH (5 ml). The reaction is heated at 50° C. for 20 hours and then allowed to cool to room temperature. The solvent is removed in vacuo and the residue dissolved in water (10 ml). The pH of the solution is adjusted to 5 using 1 M HCl and the resulting solid is collected by filtration to give the title compound 1-Diethylcarbamoylmethyl-1H-indole-4-carboxylic acid; [M+H]+ 275

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in water (10 ml)
  4. filtrationthe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-5c5e49cdc5f3468580504b37083d3614
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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