Potassium Carbonate → HCID 66885651, compound

HRID 2076010Notes

Reaction equation

HRID 2076010 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].[CH3:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:13][C:14]1[N:15]=[CH:16][N:17]([C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 178418800HCID 178418800, compound

Product 1

HCID 66885651HCID 66885651, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-cyano-4-fluoronitrobenzene (831 mg, 5 mmol), of 4-methylimidazol (821 mg, 10 mmol) and of potassium carbonate (1382 mg, 10 mmol) in acetonitrile (10 mL) was stirred over the weekend at room temperature. The solvent was evaporated and the residue was partitioned between ethyl acetate and 1N aqueous NaOH solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude product was crystallized from ethanol/water to yield the title compound (650 mg, 57%) as an off-white solid. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=8.95 (s, 1H), 8.62 (d, 1H), 8.16 (s, 1H), 7.93 (d, 1H), 7.49 (s, 1H), 2.21 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1N aqueous NaOH solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crude product was crystallized from ethanol/water

Sources & evidence

ORD record
ord-2904fe8f5f3d4e7d87c678acc8bbf6ad
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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