Potassium Carbonate → HCID 66885651, compound

HRID 1855533Notes

Reaction equation

HRID 1855533 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, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 831 mg (5 mmol) of 3-cyano-4-fluoronitrobenzene, of 0.82 g (10 mmol) 4-methylimidazol and of 1.38 g (10 mmol) potassium carbonate in acetonitrile (10 mL) was stirred for 60 h at 20° C. The solvent was evaporated and the residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate, and the solvent was evaporated under reduced pressure. The crude product was crystallized from ethanol/water yielding the title compound (0.65 g, 57%) as an off-white solid. 1H NMR (DMSO-D6, 250 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 sodium hydroxide 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 sulphate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe crude product was crystallized from ethanol/water yielding the title compound (0.65 g, 57%) as an off-white solid

Sources & evidence

ORD record
ord-685ba1af2bee49faa29dd757c6c969c6
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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