Hydrochloric Acid → HCID 23508474, compound

HRID 1883680Notes

Reaction equation

HRID 1883680 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.Cl.C(=O)([O-])O.[Na+]>CS(C)=O.O>[N:11]1[CH:12]=[CH:13][C:8]([NH:7][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 17274-AminopyridineHCID 145174-FluorobenzonitrileHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 23508474HCID 23508474, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

10 ml of dimethyl sulfoxide was added to the above potassium tert-butoxide, followed by cooling in an ice-water bath. While this mixture was kept at 20° C. or below, 1.882 g of 4-aminopyridine was added thereto, followed by stirring at room temperature for 1 hour. 1.21 g of 4-fluorobenzonitrile was dissolved in 3 ml of dimethyl sulfoxide, and this solution was added dropwise to the above reaction mixture kept at an internal temperature of 30° C. or below, followed by stirring at room temperature for 30 minutes. After water was added to the reaction mixture, the resulting mixture was acidified with dilute hydrochloric acid and then neutralized with a saturated aqueous solution of sodium hydrogen carbonate. The product was extracted with tetrahydrofuran-diethyl ether (1:1), and the organic layer was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 9:1 mixture of chloroform and methanol as the eluent) to obtain 1.85 g of 4-[N-(4-pyridyl)amino]benzonitrile.

Workup

  1. temperatureby cooling in an ice-water bath
  2. customwas kept at 20° C. or below
  3. additionthis solution was added dropwise to the above reaction mixture
  4. customkept at an internal temperature of 30° C. or below
  5. stirringby stirring at room temperature for 30 minutes
  6. extractionThe product was extracted with tetrahydrofuran-diethyl ether (1:1)
  7. washthe organic layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe resulting crude product was purified by silica gel column chromatography (
  11. additiona 9:1 mixture of chloroform and methanol as the eluent)

Sources & evidence

ORD record
ord-693c82d989ea4b689f466a1a1a1102a1
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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