Methanol → Methyl 2-(1-methyl-1H-indol-3-yl)acetate

HRID 1288649Notes

Reaction equation

HRID 1288649 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([OH:14])=[O:13])=[CH:3]1.S(=O)(=O)(O)O.[CH3:20]O>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([O:14][CH3:20])=[O:13])=[CH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2541662-(1-methyl-1H-indol-3-yl)acetic acid

Product 1

HCID 11106438Methyl 2-(1-methyl-1H-indol-3-yl)acetate

Procedure

To a solution of 20 g of 1-methyl-3-indole acetic acid in 120 mL of methanol was added 0.5 mL of concentrated sulfuric acid and the mixture was stirred at room temperature for 18 hours. The mixture was concentrated by evaporation and the residue was dissolved in dichloromethane, and then poured into a solution of aqueous saturated sodium bicarbonate. The mixture was then extracted with dichloromethane and excess magnesium sulfate was added to the extract. The product was purified by distillation to give 25 g of yellow oil.

Workup

  1. concentrationThe mixture was concentrated by evaporation
  2. dissolutionthe residue was dissolved in dichloromethane
  3. additionpoured into a solution of aqueous saturated sodium bicarbonate
  4. extractionThe mixture was then extracted with dichloromethane and excess magnesium sulfate
  5. additionwas added to the extract
  6. distillationThe product was purified by distillation

Sources & evidence

ORD record
ord-0715c72bda124bf98c74e734fd1917d1
Source dataset
uspto-grants-1998_05
Patent number
US05747236

Reaction notes

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