2-Nitropropane → 3-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole

HRID 1648391Notes

Reaction equation

HRID 1648391 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11]N(C)C.[OH-].[Na+].[N+:17]([CH:20]([CH3:22])[CH3:21])([O-:19])=[O:18]>C(O)(=O)C>[CH3:21][C:20]([CH3:22])([N+:17]([O-:19])=[O:18])[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 14798Sodium HydroxideHCID 134914391-(5-Chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

Product 1

HCID 199199343-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indoleYield 105.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

5-Chloro-3-(dimethylaminomethyl)-1H-indole (10.6 g, 50.5 mmol), prepared as in Example 2, Step (a) and powdered sodium hydroxide (3.0 g, 75.0 mmol) were combined in 2-nitropropane (80 mL, 890.8 mmol) and the mixture was stirred at 120° C. and under nitrogen for 20 hours. The mixture was cooled, acidified with 10% acetic acid (80 mL), stirred at room temperature for 1 hour, and then extracted into ether. The organic phase was separated, washed with water and then brine, dried over magnesium sulfate, and evaporated. Filtration of the residue through a short column of silica gel gave 3-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole (13.5 g, 53.1 mmol) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted into ether
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialbrine, dried over magnesium sulfate
  7. customevaporated
  8. filtrationFiltration of the residue through a short column of silica gel

Sources & evidence

ORD record
ord-2102caf230604c98ac327e7a3f369b75
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Reaction notes

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