HCID 19815911, compound → HCID 19815889, compound

HRID 2247869Notes

Reaction equation

HRID 2247869 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([CH3:16])[C:10]=2[C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>C(O)C.O1CCCC1.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([CH3:16])[C:10]=2[C:17]([OH:19])=[O:18])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 2

HCID 19815911HCID 19815911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19815889HCID 19815889, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 4-(3-cyanophenyl)-2,6-dimethyl-3-pyridinecarboxylate (0.45 g) in a mixture of ethanol (9 ml) and tetrahydrofuran (9 ml) was hydrogenated under an atmospheric pressure of hydrogen over 10% palladium charcoal (90 mg) at 60° C. for 1.5 hours. After removal of the catalyst, the solvent was evaporated in vacuo. The residue was triturated with diethyl ether and dried to give 4-(3-cyanophenyl)-2,6-dimethyl-3-pyridinecarboxylic acid (0.25 g).

Workup

  1. customAfter removal of the catalyst
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-bc11e6358582490a934e438947ef2d9e
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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