Methanol → Methyl 1H-indole-2-carboxylate

HRID 1066789Notes

Reaction equation

HRID 1066789 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[CH3:18]O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:18])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 72899Indole-2-carboxylic acid

Product 1

HCID 70992Methyl 1H-indole-2-carboxylateYield 77%

Procedure

Indole-2-carboxylic acid (47.0 g, 292 mmol) was dissolved in 200 ml of methanol. To this solution was added 6 ml of concentrated sulfuric acid. The resulting mixture was heated to reflux and maintained at this temperature for about 16 hours. The reaction mixture was then cooled to room temperature and the solids were removed by filtration and then washed with 200 ml of methanol. The crystals were dried in a vacuum oven, yielding 39.5 grams (77%) of the desired title product as white needles. Analytical data obtained was consistent with the proposed title structure.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained at this temperature for about 16 hours
  4. customthe solids were removed by filtration
  5. washwashed with 200 ml of methanol
  6. customThe crystals were dried in a vacuum oven

Sources & evidence

ORD record
ord-026438c629ef46b08e03a3b6d7c759f2
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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