Potassium Carbonate → Nonyl indole-3-carboxylate

HRID 260832Notes

Reaction equation

HRID 260832 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127421-BromononaneHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 22400454Nonyl indole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of indole-3-carboxylic acid, 1-bromononane and potassium carbonate in N,N-dimethylformamide was stirred at room temperature for 15 hours. After insoluble materials were filtered off, the filtrate was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. The solid was collected and washed with hexane to give nonyl indole-3-carboxylate.

Workup

  1. filtrationAfter insoluble materials were filtered off
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe solid was collected
  7. washwashed with hexane

Sources & evidence

ORD record
ord-a8b8a3adb2e747c7ba5353b6483eacc7
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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