Ethanol → Ethyl indole-2-carboxylate

HRID 1911783Notes

Reaction equation

HRID 1911783 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(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:11][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 73125Ethyl indole-2-carboxylateYield 85.5%

Conditions

Temperature
0 °C

Procedure

1H-indole-2-carboxylic acid (1 g, 6.2 mmol) was dissolved in 20 mL of ethanol. To this thionyl chloride (5.86 g, 49.68 mmol) was added drop wise with stirring at 0° C and stirring was continued for 30 h at room temperature. Excess of SOCl2 was evaporated, water was added to the residue and the suspension was filtered to afford the title compound (1.0 g, yield: 85.5%).

Workup

  1. stirringstirring
  2. customExcess of SOCl2 was evaporated
  3. additionwater was added to the residue
  4. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-f3504bdf99df4562a9a8748e1fa9b860
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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