Methanol → Methyl 3-(1H-indol-3-yl)propanoate

HRID 1822879Notes

Reaction equation

HRID 1822879 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1.S(=O)(=O)(O)O.O.[NH4+].[CH3:22]O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([O:14][CH3:22])=[O:13])=[CH:2]1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 37441H-Indole-3-propanoic acidHCID 22024077Azanium;hydrate

Product 1

HCID 21711Methyl 3-(1H-indol-3-yl)propanoateYield 93%

Conditions

Temperature
0 °C

Procedure

2 g (10.57 mmol) of 3-indolepropionic acid were dissolved in 50 ml of methanol. The solution was cooled to 0° C. and 5 ml of sulfuric acid 96% were dropped under stirring. The solution was maintained at room temperature overnight and then poured onto ice-water, basified with 30% ammonium hydrate and finally extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give 2.3 g of an oily product (93% yield).

Workup

  1. temperatureThe solution was maintained at room temperature overnight
  2. additionpoured onto ice-water
  3. extractionfinally extracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-11b2a204ecee4c81a747ba6a4c763911
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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