Ethanol → Methyl 2-propylindole-6-carboxylate

HRID 278090Notes

Reaction equation

HRID 278090 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH2:14][C:15](=O)[CH2:16][CH2:17][CH3:18])[C:7]([O:9][CH3:10])=[O:8])([O-])=O.C(O)C.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1>[CH2:16]([C:15]1[NH:1][C:4]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=2)[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24489Sodium DithioniteHCID 22627364Methyl 3-nitro-4-(2-oxopentyl)benzoate

Product 1

HCID 22627295Methyl 2-propylindole-6-carboxylateYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-nitro-4-(2-oxopentyl)benzoate (114 mg) in a mixture of tetrahydrofuran (1.5 ml), ethanol (1.5 ml) and water (2.1 ml) was added sodium hydrosulfite (3.0 g), and the mixture was stirred under reflux for 30 minutes. The resulting mixture was evaporated in vacuo, and the residue was diluted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by thin layer chromatography with a mixture of hexane and ethyl acetate (2:1) to give methyl 2-propylindole-6-carboxylate (54.6 mg).

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe resulting mixture was evaporated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by thin layer chromatography with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-16acf8988a2d45feaa793baed73d9147
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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