Sodium hydride → HCID 18973467, compound

HRID 2394399Notes

Reaction equation

HRID 2394399 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[CH:5]=[CH:4]1.[CH2:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[CH2:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:3]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=3[CH:5]=[CH:4]2)=[O:23])=[CH:20][CH:19]=1)[CH3:17]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 853684-Ethylbenzoyl chlorideHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 18973467HCID 18973467, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (95%; 0.30 g) was suspended in 10 ml of dimethylformamide and the suspension was stirred while cooling the same at a temperature ranging from 0° to 5° C. To this mixed liquid, there was dropwise added a solution of 2.00 g of methyl indole-4-carboxylate in 5 ml of dimethylformamide over 15 minutes. After the completion of the dropwise addition, the reaction solution was stirred at a temperature ranging from 0° to 5° C. for 30 minutes. To the reaction solution, there was added a solution of 2.09 g of 4-ethylbenzoyl chloride in 5 ml of dimethylformamide, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 200 ml of a 10% ammonium chloride aqueous solution, followed by extraction with ethyl acetate (200 ml×2). The extract was washed with a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through distillation under reduced pressure to thus give 3.51 g of a residue. The residue was purified by silica gel chromatography (hexane:ethyl acetate=11:1) to give 2.18 g of methyl 1-(4-ethylbenzoyl)indole-4-carboxylate as colorless crystals. The yield thereof was found to be 62%.

Workup

  1. temperaturewhile cooling the same at a temperature
  2. customranging from 0° to 5° C
  3. additionAfter the completion of the dropwise addition
  4. stirringthe reaction solution was stirred at a temperature
  5. stirringby stirring at room temperature for 2 hours
  6. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  7. washThe extract was washed with a saturated common salt solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed through distillation under reduced pressure to thus give 3.51 g of a residue
  10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=11:1)

Sources & evidence

ORD record
ord-298c8e4b135047b5942951a5173a60cf
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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