Ethanol → Ethyl 5-methoxyindole-2-carboxylate

HRID 131640

Reaction equation

HRID 131640 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([OH:18])=[O:17])=[CH:10]2.[CH2:19](O)[CH3:20]>>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10]2

Participants

4

Reactant 3

HCID 702EthanolHCID 204015-Methoxyindole-2-carboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 20926Ethyl 5-methoxyindole-2-carboxylate

Procedure

1.91 ml (26.15 mmol) of thionyl chloride are added dropwise with stirring at 0° C. to a solution of 1 g (5.23 mmol) of 5-methoxy-1H-indole-2-carboxylic acid in 52 ml of ethanol. The reaction mixture is heated at reflux for 2 hours and then it is cooled and concentrated under reduced pressure. The residue is taken up in 100 ml of ethyl acetate and this solution is washed with two times 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The solution is dried over magnesium sulfate and filtered, and then the filtrate is concentrated under reduced pressure. 1.2 g of product are obtained, which product is used as is in the following stage.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperatureit is cooled
  4. concentrationconcentrated under reduced pressure
  5. washthis solution is washed with two times 50 ml of water
  6. dry with materialThe solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ac5f0b55df74141adc979b89387f066
Source dataset
uspto-grants-2008_06
Patent number
US07384969B2

Linked notes

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