Hydrochloric Acid → [2,4'-Bipyridine]-5-carboxylic acid hydrochloride

HRID 1060991Notes

Reaction equation

HRID 1060991 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.C(B(CC)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)C.Cl.[K].Cl>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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.O>[ClH:1].[N:17]1[CH:18]=[CH:19][C:14]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)=[CH:15][CH:16]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 792226-Chloronicotinic acidHCID 133188714-(Diethylboranyl)pyridineHCID 86590535Potassium hydrochloride

Product 1

HCID 69483715[2,4'-Bipyridine]-5-carboxylic acid hydrochloride

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In tetrahydrofuran (20 ml), 6-chloronicotinic acid (535 mg) and diethyl (4-pyridyl)borane (500 mg) were dissolved. To the resulting solution, tetrabutylammonium bromide (546 mg), potassium hydrochloride (570 mg), tetrakis(triphenylphosphine)palladium (0) (392 mg) and water (0.5 ml) were added, followed by heating under reflux for 6 hours. Dilute hydrochloric acid was added to the reaction mixture to make it acidic. Water and ethyl acetate were poured into the resulting mixture for extraction. The water layer so extracted was distilled off under reduced pressure. The residue was purified by chromatography through a synthetic adsorbent (“Diaion HP-20”, water ˜50% acetonitrile-water). To the resulting fraction, dilute hydrochloric acid was added to make it acidic. The solvent was then distilled off. Tetrahydrofuran was added to the residue and the precipitate was collected by filtration, whereby the title compound (269 mg, 32%) was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. extractionThe water layer so extracted
  4. distillationwas distilled off under reduced pressure
  5. customThe residue was purified by chromatography through a synthetic adsorbent (“Diaion HP-20”, water ˜50% acetonitrile-water)
  6. additionTo the resulting fraction, dilute hydrochloric acid was added
  7. distillationThe solvent was then distilled off
  8. additionTetrahydrofuran was added to the residue
  9. filtrationthe precipitate was collected by filtration, whereby the title compound (269 mg, 32%)
  10. customwas obtained

Sources & evidence

ORD record
ord-6a0388fb746c4487ba703516b852bac1
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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