Potassium Carbonate → HCID 66810384, compound

HRID 1097485Notes

Reaction equation

HRID 1097485 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[NH2:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[F:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[F:20])[O:21][C:8]1[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 135191803-Amino-4-fluorophenol

Product 1

HCID 66810384HCID 66810384, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyano-4-fluoronitrobenzene (9.36 g, 56.3 mmol) and 3-amino-4-fluorophenol (7.16 g, 56.3 mmol) in N,N-dimethylformamide (150 ml) was added potassium carbonate (11.7 g, 84.5 mmol), and the mixture was stirred at room temperature for 4 hr. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. 5% Aqueous sodium hydrogen carbonate solution (300 mL) was added to the residue, and the mixture was extracted with ethyl acetate (270 mL)/tetrahydrofuran (30 mL). The aqueous layer was extracted with ethyl acetate (270 mL)/tetrahydrofuran (30 mL), and the combined organic layer was washed with saturated brine (300 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was purified by basic silica gel column chromatography (eluate: ethyl acetate). The obtained solution was concentrated under reduced pressure to give the title compound (15.6 g, quantitative) as a beige powder.

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. addition5% Aqueous sodium hydrogen carbonate solution (300 mL) was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (270 mL)/tetrahydrofuran (30 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (270 mL)/tetrahydrofuran (30 mL)
  6. washthe combined organic layer was washed with saturated brine (300 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationInsoluble material was filtered off
  9. customthe filtrate was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  10. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-16577f02638a4a47982b97a13ae1843a
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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