Sodium Hydroxide → HCID 22627515, compound

HRID 278086Notes

Reaction equation

HRID 278086 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=2)[NH:10][CH:9]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22627482HCID 22627482, compound

Product 1

HCID 22627515HCID 22627515, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 3-(3-methoxycarbonylpropyl)-indole-6-carboxylate (656 mg) in methanol (24 ml) was added 1N aqueous sodium hydroxide (2.46 ml), and the mixture was stirred at 20° C. for 2 days. The resulting mixture was evaporated in vacuo, and the residue was acidified with 1N hydrochloric acid (2.6 ml) and extracted with ethyl acetate. The organic chase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with ether to give methyl 3-(3-carboxypropyl)indole-6-carboxylate (486 mg) as solid.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic chase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-35f3b809e0004964a67ba9a48eb98cc3
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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