Thionyl Chloride → Butyl 7-methoxy-1H-indole-2-carboxylate

HRID 1762933Notes

Reaction equation

HRID 1762933 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:4]([O:13][C:12]([C:9]1[NH:10][C:11]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[CH:4][C:3]=2[O:2][CH3:1])=[O:14])[CH2:3][CH2:11][CH3:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1681875-Methoxyindole-2-carboxylic acid

Product 1

HCID 13089716Butyl 7-methoxy-1H-indole-2-carboxylateYield 105.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 6.0 g of 7-methoxyindole-2carboxylic acid in 100 ml of toluene is combined with 4.3 ml of thionyl chloride; the mixture is heated under stirring for 3 hours to 90° C., then concentrated under vacuum. The residue is combined with 50 ml of n-butanol and heated for one hour under reflux Then the mixture is evaporated to dryness under vacuum, the oily residue is boiled with 60 ml of petroleum ether, the clear solution is decanted from the dark residue, and cooling of the solution yields 4.1 g of 7-methoxyindole-2-carboxylic acid n-butyl ester, mp 66°-69° C.

Workup

  1. temperaturethe mixture is heated
  2. concentrationconcentrated under vacuum
  3. temperatureheated for one hour
  4. temperatureunder reflux
  5. customthe mixture is evaporated to dryness under vacuum
  6. customthe clear solution is decanted from the dark residue
  7. temperaturecooling of the solution

Sources & evidence

ORD record
ord-8f47fd815f2a4ae19a3b534dd8a00920
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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