Hydrochloric Acid → 4-(Pyridin-4-yl)benzoic acid hydrochloride

HRID 1060989Notes

Reaction equation

HRID 1060989 reaction equation
[ClH:1].Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:9]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)([OH:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[ClH:1].[N:6]1[CH:7]=[CH:8][C:3]([C:15]2[CH:16]=[CH:17][C:12]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=2)=[CH:4][CH:5]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 574326074-(Pyridin-4-yl)benzoic acid hydrochloride

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent3×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

At room temperature, 4-bromopyridine hydrochloride (11.7 g) and 4-carboxybenzeneboronic acid (10.0 g) were dissolved in toluene (250 ml) and water (250 ml). To the resulting solution, tetrakis(triphenylphosphine)palladium (O) (5.00 g) and anhydrous sodium carbonate (25.4 g) were added successively, followed by refluxing under heat at 120° C. for 19 hours. After allowed to cool down, the reaction mixture was added with ethyl acetate and water, whereby the water layer was separated. The organic layer was extracted twice with water. All the water layers so obtained were combined and to the resulting solution, concentrated hydrochloric acid was added to make it acidic, followed by washing with ethyl acetate again. The solvent was distilled off from the water layer until it decreased to 100 ml. The colorless solid so precipitated was collected by filtration and dried under reduced pressure, whereby the title compound (8.37 g, 59%) was obtained.

Workup

  1. temperatureby refluxing
  2. temperatureto cool down
  3. customwas separated
  4. extractionThe organic layer was extracted twice with water
  5. customAll the water layers so obtained
  6. additionwas added
  7. washby washing with ethyl acetate again
  8. distillationThe solvent was distilled off from the water layer until it
  9. customThe colorless solid so precipitated
  10. filtrationwas collected by filtration
  11. dry with materialdried under reduced pressure, whereby the title compound (8.37 g, 59%)
  12. customwas obtained

Sources & evidence

ORD record
ord-2d51245ed00b4338ad88a43600fcc640
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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