Water → 1-Methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide

HRID 230549Notes

Reaction equation

HRID 230549 reaction equation
[H-].[Na+].[I-].[CH4:4].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1)([O-:7])=[O:6].O>CN(C)C=O>[CH3:4][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=2)=[C:15]1[C:23]([NH2:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 20975526HCID 20975526, compoundHCID 577628413-(4-Nitrophenyl)-1H-indole-2-carboxamide

Product 1

HCID 688244991-Methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.047 g of sodium hydride and then 73 μl of methane iodide are added to a solution of 0.3 g of 3-(4-nitro-phenyl)-1H-indole-2-carboxamide in 8 ml of anhydrous dimethylformamide under argon. The reaction mixture is stirred at ambient temperature for 2 hours and 45 ml of water are added. The solid formed is filtered off, washed with 3 times 15 ml of water, and filter-dried. After drying under vacuum, 0.22 g of 1-methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide are obtained, the characteristics of which are as follows:

Workup

  1. customThe solid formed
  2. filtrationis filtered off
  3. washwashed with 3 times 15 ml of water
  4. customfilter-dried
  5. dry with materialAfter drying under vacuum, 0.22 g of 1-methyl-3-(4-nitrophenyl)-1H-indole-2-carboxamide
  6. customare obtained

Sources & evidence

ORD record
ord-541512b6400f454a88d09fb861984f4f
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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