Methanol → Methyl indole-6-carboxylate

HRID 853719Notes

Reaction equation

HRID 853719 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O.[CH3:15]O.[H][H]>C(OCC)(=O)C.[C].[Pd]>[NH:12]1[C:3]2[C:2](=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)[CH:1]=[CH:15]1

Participants

6

Reactant 3

HCID 887MethanolHCID 81816Methyl 4-methyl-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 639844Methyl indole-6-carboxylateYield 68.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a reaction flask were introduced 87.1 g of methyl 4-methyl-3-nitrobenzoate, 400 ml of methanol and 8 g of 5% palladium-carbon (Pd/C). The content of the flask was stirred at room temperature for 12 hours in an atmosphere of hydrogen at ordinary pressure. The Pd/C was removed by filtration, and methanol was distilled out from the filtrate to obtain a slightly yellow colored solid product. The product was dissolved in ethyl acetate, washed with 5% aqueous solution of NaOH, washed with 5% aqueous solution of hydrochloric acid and water, and the ethyl acetate was distilled off. Thus, 50.4 g (yield 68.7%) of methyl indole-6-carboxylate monomer was obtained.

Workup

  1. customThe Pd/C was removed by filtration, and methanol
  2. distillationwas distilled out from the filtrate
  3. customto obtain a slightly yellow colored solid product
  4. washwashed with 5% aqueous solution of NaOH
  5. washwashed with 5% aqueous solution of hydrochloric acid and water
  6. distillationthe ethyl acetate was distilled off

Sources & evidence

ORD record
ord-d05e92ebd70c40659c1c8c927c30d15f
Source dataset
uspto-grants-2007_08
Patent number
US07255779B2

Reaction notes

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