Sodium hydride → Ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate

HRID 565040Notes

Reaction equation

HRID 565040 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

Product 1

HCID 21194137Ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 0.42 g (1.64 mmol) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.066 g (1.64 mmol) of 60% sodium hydride and 5 ml of dimethylformamide, the suspension was stirred at room temperature until the mixture became an almost transparent solution. Then 0.35 g (2.49 mmol) of 1-fluoro-2-nitrobenzene was added to the solution at room temperature followed by stirring for 5 hours at the same temperature. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 0.53 g (94.3%) of ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate.

Workup

  1. stirringby stirring for 5 hours at the same temperature
  2. additionThe reaction mixture was poured onto ice water
  3. extractionThe resulting mixture was then extracted three times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was isolated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb4a6048ed284f78a01b609b5489867d
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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