Hydrochloric Acid → HCID 23004093, Verbindung

HRID 1709816

Reaktionsgleichung

Reaktionsgleichung von HRID 1709816
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:20]>[Pd].C(O)(=O)C.CO.C(#N)C>[ClH:20].[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 772524-Benzhydrylpyridine

Produkt 1

HCID 23004093HCID 23004093, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 21959252Acetonitrile methanolLösungsmittel

Versuchsvorschrift

A mixture of 62.69 g (0.256 mole) of diphenyl-4-pyridylmethane and 6.4 g of 10% palladium on carbon (0.0060 mole) in 300 ml of glacial acetic acid and under an atmosphere of hydrogen (44 psi) was shaken on a Parr apparatus at 865° for 4 days. The reaction mixture was filtered, and the solvent was removed in vacuo from the filtrate. The residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give a solid. This was dissolved in a mixture of methanol-acetonitrile, and excess ethereal hydrogen chloride was added. A precipitate was collected to give 59.13 g (80.3%) of slightly impure title compound as a white, crystalline solid, m.p. 273°-274° C. Part of this was recrystallized from methanol-ether to give an analytically pure sample, m.p. 275.5°-277° C.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo from the filtrate
  3. customThe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give a solid
  7. additionwas added
  8. customA precipitate was collected

Quellen und Nachweise

ORD-Eintrag
ord-fab04107275b4890aeb9f104e17555f5
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04950674

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