Dimethylformamide → 6-Nitro-1H-indole-3-carbonitrile

HRID 1529623Notes

Reaction equation

HRID 1529623 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(O)=O.[Na+].[CH3:18][N:19](C=O)C>CC#N>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:18]#[N:19])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 785026-Nitro-1H-indoleHCID 516892Sodium Bicarbonate

Product 1

HCID 2831796-Nitro-1H-indole-3-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-nitroindole (4.86 g 30 mmol) in DMF (24.3 mL) and CH3CN (243 mL) was added dropwise a solution of C1SO2NCO (5 mL, 57 mmol) in CH3CN (39 mL) at 0° C. After addition, the reaction was allowed to warm to room temperature and stirred for 2 h. The mixture was poured into ice-water, basified with sat. NaHCO3 solution to pH 7-8 and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give 6-nitro-1H-indole-3-carbonitrile (4.6 g, 82%).

Workup

  1. additionAfter addition
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f587edf144e4b1db10627f8a0be8d81
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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