HCID 54356080, compound → HCID 14835657, compound

HRID 1709236Notes

Reaction equation

HRID 1709236 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[CH:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1>C(O)C.Cl.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:17][CH:18]=1

Participants

5

Reactant 1

HCID 54356080HCID 54356080, compound

Product 1

HCID 14835657HCID 14835657, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

9.56 g of 2-(p-methylstyryl)nicotinic acid was dissolved in 190 ml of ethanol and 3.3 ml of concentrated hydrochloric acid. To the solution was added 1.00 g of 5% palladium-carbon (catalyst), and the mixture was subjected to hydrogenation at 40° C. at atmospheric pressure. The reaction mixture was filtered to remove the catalyst, and the filtrate was subjected to distillation under reduced pressure to remove the solvent. To the resulting residue was added 100 ml of water and the mixture was adjusted to pH 5.0 with a 10% aqueous sodium hydroxide solution. The resulting crystals were collected by filtration and dried to obtain 8.58 g of 2-(p-methylphenethyl)nicotinic acid. It was recrystallized from ethanol to obtain 7.72 g of colorless crystals having a melting point of 172°-173° C.

Workup

  1. customwas subjected to hydrogenation at 40° C. at atmospheric pressure
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. distillationthe filtrate was subjected to distillation under reduced pressure
  5. customto remove the solvent
  6. additionTo the resulting residue was added 100 ml of water
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-1fe6d715b1bf4e62bdd4ca2feb11926a
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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