Dimethylformamide → 1-benzoyl-5-nitro-1H-indole

HRID 1359136Notes

Reaction equation

HRID 1359136 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OC(=O)C)C.O>[C:24]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 225235-Nitroindole

Product 1

HCID 98350711-benzoyl-5-nitro-1H-indoleYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-nitroindole (50 mg, 0.31 mmol) and potassium carbonate (128 mg, 0.93 mmol) were suspended in. dimethylformamide (1.0 ml). Then, benzoyl chloride (0.04 ml, 0.345 mmol) was added and stirred at room temperature for 2 hours. After completing the reaction, water and ethylacetate (respectively 5 ml) were added to extract, washed with brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then purified through a flash column chromatography (an eluent: ethyl acetate/n-hexane=1/1, v/v). As a result, the present compound (35 mg, productive yield 43%) was obtained.

Workup

  1. additionwere added
  2. extractionto extract
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified through a flash column chromatography (an eluent
  7. customAs a result, the present compound (35 mg, productive yield 43%) was obtained

Sources & evidence

ORD record
ord-092f7dd971b04a06bafe369d44aa98ba
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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