Methyl 2-nitro-3-(2-oxo-n-propyl)benzoate → methyl 2-methyl-1H-indole-7-carboxylate

HRID 274574Notes

Reaction equation

HRID 274574 reaction equation
[N+:1]([C:4]1[C:13]([CH2:14][C:15](=O)[CH3:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O>C1COCC1.[Pd]>[CH3:16][C:15]1[NH:1][C:4]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 20093000Methyl 2-nitro-3-(2-oxo-n-propyl)benzoate

Product 1

HCID 12230325methyl 2-methyl-1H-indole-7-carboxylateYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of methyl 2-nitro-3-(2-oxo-n-propyl)benzoate (0.33 g) and 10% Pd/C (50% wet, 0.33 g) in THF (20 ml) was stirred under H2 atmosphere at room temperature for 2.5 hours. After removal of insoluble materials by filtration, the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to give methyl 2-methylindole-7-carboxylate as a pale yellow syrup (0.225 g).

Workup

  1. customAfter removal of insoluble materials
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ca9d26e698144086adaec5faa9e51c5b
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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