Sulfuric Acid → Methyl 5-methyl-1H-indole-2-carboxylate

HRID 2185695Notes

Reaction equation

HRID 2185695 reaction equation
[CH3:1][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.[C:19](=O)([O-])O.[Na+]>CO>[CH3:1][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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 2591885-methyl-1H-indole-2-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 4777680Methyl 5-methyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methylindole-2-carboxylic acid (0.9 g, 5.13 mmol) was dissolved in methanol (25 ml) and treated with sulphuric acid (0.5 ml). The mixture was refluxed for 4 h. The volume of solvent was reduced and the residue treated with sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic fractions were dried and concentrated to give the desired ester.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. extractionextracted with ethyl acetate
  3. customThe organic fractions were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5871be7d1e8a4fd4be422c95a959837e
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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