Dimethylformamide → HCID 19600392, compound

HRID 609762Notes

Reaction equation

HRID 609762 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.CN(C)C=O.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[C:31]2[C:26](=[CH:27][C:28]([N+:32]([O-:34])=[O:33])=[CH:29][CH:30]=2)[CH:25]=[CH:24]1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:20][CH2:21][CH2:22][N:23]1[C:31]3[C:26](=[CH:27][C:28]([N+:32]([O-:34])=[O:33])=[CH:29][CH:30]=3)[CH:25]=[CH:24]1)[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 138725-MethoxyindoleHCID 24758Sodium hydrideHCID 11172472HCID 11172472, compound

Product 1

HCID 19600392HCID 19600392, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 926 mg of 5-methoxyindole was added 30 ml of dimethylformamide and 230 mg of sodium hydride (in oil), this mixture was stirred under nitrogen gas stream at 60° C. for 1 hour. Then 1.5 g of 1-(3-chloropropyl)-5-nitroindole was added to the reaction mixture and stirred at room temperature overnight. The reaction mixture was further stirred at 60° C. for 5.5 hours, then water was added thereto, and the crystals being separated were collected by filtration, and washed with water. The washed crystals were subjected to a silica gel column chromatography (eluent: dichloromethane), there was obtained 1.8 g of 1-[3-(5-methoxyindol-1-yl)propyl]-5-nitroindole as in the form of yellow powdery product.

Workup

  1. stirringstirred at room temperature overnight
  2. stirringThe reaction mixture was further stirred at 60° C. for 5.5 hours
  3. customthe crystals being separated
  4. filtrationwere collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-922513262e53436583451eb6ff72d03b
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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