Potassium Carbonate → HCID 9283383, compound

HRID 242904Notes

Reaction equation

HRID 242904 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 167023-AminobenzonitrileHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 9283383HCID 9283383, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 1-fluoro-2-nitrobenzene (2.00 g, 14.2 mmol), 3-aminobenzonitrile (3.35 g, 28.3 mmol) and potassium carbonate (5.88 g, 42.5 mmol) in DMF (30 mL) was stirred at 135° C. for 16 h under a nitrogen atmosphere. After cooling to RT, the reaction mixture was partitioned between DCM and water. The aqueous phase was extracted with DCM (×3) and the combined organic fractions dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 25-100% DCM in cyclohexane) then loaded onto an SCX-2 cartridge and washed with DCM to afford 3-(2-nitrophenylamino)benzonitrile as a bright orange foam (2.02 g, 60%).

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between DCM and water
  3. extractionThe aqueous phase was extracted with DCM (×3)
  4. dry with materialthe combined organic fractions dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 25-100% DCM in cyclohexane)
  7. washwashed with DCM

Sources & evidence

ORD record
ord-4d8d500fd06845a68b62fd328eab5ab6
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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