Methanol → Methyl 5-chloro-1H-indole-2-carboxylate

HRID 2185698Notes

Reaction equation

HRID 2185698 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.S(=O)(=O)(O)O.[CH3:19]O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH3:19])=[O:12])=[CH:5]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 826935-Chloro-1H-indole-2-carboxylic acid

Product 1

HCID 4777711Methyl 5-chloro-1H-indole-2-carboxylate

Procedure

5-Chloroindole-2-carboxylic acid (0.95 g, 4.65 mmol) was dissolved in methanol (35 ml) and treated with sulphuric acid (0.5 ml). The mixture was refluxed for 5 h and cooled and the solvent was removed. The residue was recrystallized twice from methanol to give the product.

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. temperaturecooled
  3. customthe solvent was removed
  4. customThe residue was recrystallized twice from methanol
  5. customto give the product

Sources & evidence

ORD record
ord-1843d09476d94f2d81b51943c44e87d1
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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