Methanol → methyl 4-methyl-1H-indole-2-carboxylate

HRID 1066857Notes

Reaction equation

HRID 1066857 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]2.S(=O)(=O)(O)O.[CH3:19]O>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:19])=[O:12])[NH:6]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 39260874-Methyl-1H-indole-2-carboxylic acid

Product 1

HCID 4714967methyl 4-methyl-1H-indole-2-carboxylate

Procedure

Under an argon atmosphere 4-methyl-1H-indole-2-carboxylic acid (0.64 g, 3.65 mmol) was dissolved in 20 ml of methanol. Concentrated sulfuric acid (0.5 ml) was added and the resulting mixture was heated to reflux and maintained at this temperature overnight. The progress of the reaction was monitored by thin layer chromatography. Some solvent was removed in vacuo and the resulting crystals were removed by filtration. The solids were taken up in diethyl ether, washed twice with saturated sodium bicarbonate, and then once with brine. The organic fraction was dried over magnesium sulfate and the solvents were removed in vacuo.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained at this temperature overnight
  4. customSome solvent was removed in vacuo
  5. customthe resulting crystals were removed by filtration
  6. washwashed twice with saturated sodium bicarbonate
  7. dry with materialThe organic fraction was dried over magnesium sulfate
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f814c765408a49ffaf5bfcb2fc2bba02
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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