Hydrochloric Acid → HCID 23004093, compound

HRID 1193638

Reaction equation

HRID 1193638 reaction equation
[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>[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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 772524-Benzhydrylpyridine

Product 1

HCID 23004093HCID 23004093, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

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 85° 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 methanolacetronitrile, and excess ethereal hydrogen chloride was added. A precipitated 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.

Workup

  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 precipitated was collected

Sources & evidence

ORD record
ord-fc6ea4127fdf48ed8727917c3e8beabc
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Linked notes

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