Phenyl Methylcarbamate → N1-Methyl-5-nitro-1H-1-indolecarboxamide

HRID 2215599Notes

Reaction equation

HRID 2215599 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([O-:5])=[O:4].[CH3:15][NH:16][C:17](=O)[O:18]C1C=CC=CC=1>CN(C)C=O>[CH3:15][NH:16][C:17]([N:11]1[C:12]2[C:8](=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:14][CH:13]=2)[CH:9]=[CH:10]1)=[O:18]

Participants

5

Reactant 3

HCID 16034Phenyl MethylcarbamateHCID 225235-NitroindoleHCID 24758Sodium hydride

Product 1

HCID 21949157N1-Methyl-5-nitro-1H-1-indolecarboxamideYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 228 mg, 5.7 mmol) was gradually added to a N,N-dimethylformamide (0.5 ml) solution of 5-nitroindole (0.841 g, 5.19 mmol) while stirring at room temperature; phenyl N-methylcarbamate (1.02 g, 6.74 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate. This was concentrated under reduced pressure; and the residue was purified by silica gel column chromatography (hexane-ethyl acetate, sequentially ethyl acetate) to yield the title compound (600 mg).

Workup

  1. stirringand the reaction mixture was stirred overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washand the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. customand the residue was purified by silica gel column chromatography (hexane-ethyl acetate, sequentially ethyl acetate)

Sources & evidence

ORD record
ord-2ffb77db021b4ed2b0b61c1a42670fac
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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