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

HRID 352720ノート

反応式

HRID 352720 の反応式
[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(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 74236Tetrabutylammonium Bromide触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In tetrahydrofuran (20 ml), 6-chloronicotinic acid (535 mg) and diethyl (4-pyridyl)borane (Chem. Pharm. Bull., 33, 4755, 1985) (500 mg) were dissolved. To the resulting solution, tetrabutylammonium bromide (546 mg), potassium hydrochloride (570 mg), tetrakis(triphenylphosphine) palladium (O) (392 mg) and water (0.5 ml) were added under an argon atmosphere, 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.

後処理

  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

出典と根拠

ORDレコード
ord-8bae588d0913494f915dc5c67aa68d21
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

反応ノート

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