Dimethylformamide → methyl 1H-indole-5-carboxylate

HRID 2187744Notes

Reaction equation

HRID 2187744 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([OH:3])=[O:2].[C:13](=O)([O-])O.[Na+].CI.CN(C)C=O>C(OCC)(=O)C.O>[CH3:13][O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)=[O:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 742801H-Indole-5-Carboxylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 2737635methyl 1H-indole-5-carboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-carboxyindole (16.0 g), sodium hydrogencarbonate (26.68 g), methyl iodide (61.11 g) and N,N-dimethylformamide (30 ml) is stirred at room temperature for 4 days. Water and ethyl acetate are added thereto for liquid-liquid separation. The organic layer is washed with aqueous sodium hydrogencarbonate, dried and concentrated to obtain 5-(methoxycarbonyl)indole (13.74 g).

Workup

  1. customfor liquid-liquid separation
  2. washThe organic layer is washed with aqueous sodium hydrogencarbonate
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dcfc883d524b4b3d843979a45246ca43
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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