Methanol → N1-Methyl-5-amino-1H-1-indolecarboxamide

HRID 2376925Notes

Reaction equation

HRID 2376925 reaction equation
CO.[Cl-].[NH4+].[CH3:5][NH:6][C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)=[O:8]>[Fe].O>[CH3:5][NH:6][C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)=[O:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 21949157N1-Methyl-5-nitro-1H-1-indolecarboxamide

Product 1

HCID 21949101N1-Methyl-5-amino-1H-1-indolecarboxamideYield 76%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Methanol (6 ml), water (2 ml), iron (0.32 g) and ammonium chloride (0.64 g) were added to N1-methyl-5-nitro-1H-1-indolecarboxamide (0.32 g, 1.46 mmol) synthesized in Production example 218-1; and the reaction mixture was heated to reflux for 2 hours. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The residue was filtrated with celite, and concentrated under reduced pressure to yield the title compound (210 mg).

Workup

  1. customsynthesized in Production example 218-1
  2. temperatureand the reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe residue was filtrated with celite
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04faaaff43d3457f9820bf0ed779139e
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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