Ethanol → Methyl indole-6-carboxylate

HRID 1808323Notes

Reaction equation

HRID 1808323 reaction equation
S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].CN(C)[CH:13]=[CH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=1[N+:24]([O-])=O.[CH2:28](O)C.O>C1COCC1.ClCCl>[NH:24]1[C:16]2[C:15](=[CH:23][CH:22]=[C:18]([C:19]([O:21][CH3:28])=[O:20])[CH:17]=2)[CH:14]=[CH:13]1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 146045Sodium dithionateHCID 73412750HCID 73412750, compound

Product 1

HCID 639844Methyl indole-6-carboxylateYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium dithionate (164.4 g; 16 equiv.) was added over a period of 20 minutes to a solution of 4-(2-(dimethylamino)vinyl)-3-nitrobenzoic acid (14 g; 1 equiv.) in a mixture of THF (42 ml), ethanol (42 ml) and water (140 ml). The reaction mixture was heated for 90 min. at reflux and then stirred for 12 hours at room temperature. When the conversion was complete, dichloromethane was added, the phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel, 10% ethyl acetate/hexane). Methyl 1H-indole-6-carboxylate (8 g; 40%) was obtained in the form of a solid.

Workup

  1. temperatureThe reaction mixture was heated for 90 min.
  2. temperatureat reflux
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customAfter removal of the solvent
  7. customunder reduced pressure, purification

Sources & evidence

ORD record
ord-36eaaac1273340c79d39205074230d93
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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