Ethyl Acetate → 4-(Pyridin-4-yl)benzoic acid hydrochloride

HRID 902860Notes

Reaction equation

HRID 902860 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](OB(O)O)=[CH:14][CH:13]=1)([OH:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>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>[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

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 227099914-Carboxyphenylboric acid

Product 1

HCID 574326074-(Pyridin-4-yl)benzoic acid hydrochlorideYield 64.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromopyridine hydrochloride (11.7 g) and 4-carboxyphenylboric acid (10.0 g) were dissolved in a mixed solvent of toluene (250 ml) and water (250 ml), tetrakis(triphenylphosphine)palladium(0) (5.0 g) and anhydrous sodium carbonate (25.4 g) were successively added, and the mixture was heated under reflux at 120° C. for 19 hours. After the reaction mixture was cooled to room temperature, ethyl acetate was added to the reaction mixture to extract it with water. Concentrated hydrochloric acid was added to the water layer to acidify it. The water layer was washed with ethyl acetate and then concentrated, and solids deposited were collected to obtain the title compound (8.37 g).

Workup

  1. additionwere successively added
  2. temperaturethe mixture was heated
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. extractionto extract it with water
  5. additionConcentrated hydrochloric acid was added to the water layer
  6. washThe water layer was washed with ethyl acetate
  7. concentrationconcentrated
  8. customsolids deposited were collected

Sources & evidence

ORD record
ord-bcb80fad52614277a4031695834abf5e
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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