Potassium Carbonate → HCID 44579953, compound

HRID 1097446Notes

Reaction equation

HRID 1097446 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 44579953HCID 44579953, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-fluoro-5-nitrobenzonitrile (5.00 g, 30.1 mmol) and 3-aminophenol (3.28 g, 30.1 mmol) in N,N-dimethylformamide (30 ml) was added potassium carbonate (6.23 g, 45.2 mmol), and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off and washed with ethyl acetate (150 mL). The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL), washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), successively, and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80→70/30) and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (5.09 g, 66%) as a yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. washwashed with ethyl acetate (150 mL)
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with ethyl acetate (200 mL)
  6. washwashed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  7. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  8. filtrationInsoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80→70/30)
  11. concentrationthe obtained solution was concentrated under reduced pressure
  12. customThe residue was crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d6cd1a36dcaf4fadbfcb87a560a0d4d3
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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