3-Benzyloxy-4-methoxy-4'-phenoxypicolinanilide → 3-Hydroxy-4-methoxy-4'-phenoxypicolinanilide

HRID 350640Notes

Reaction equation

HRID 350640 reaction equation
C([O:8][C:9]1[C:10]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[O:18])=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1>[C].[Pd].C(O)C>[OH:8][C:9]1[C:10]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[O:18])=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 178176673-Benzyloxy-4-methoxy-4'-phenoxypicolinanilide

Product 1

HCID 112445943-Hydroxy-4-methoxy-4'-phenoxypicolinanilideYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

3-Benzyloxy-4-methoxy-4′-phenoxypicolinanilide (0.64 g, 1.5 mmol) was mixed with ethanol (4 ml) to prepare a suspension. To this suspension was added 64 mg of 10% palladium-carbon. The mixture was subjected to catalytic reduction under atmospheric conditions overnight. The reaction solution was filtered, and the filtrate was concentrated under the reduced pressure. The residue was dissolved in a water-methanol mixed solution, and was recrystallized to give 0.41 g (yield 81%) of the title compound.

Workup

  1. customto prepare a suspension
  2. customwas subjected to catalytic reduction under atmospheric conditions overnight
  3. filtrationThe reaction solution was filtered
  4. concentrationthe filtrate was concentrated under the reduced pressure
  5. dissolutionThe residue was dissolved in a water-methanol mixed solution
  6. customwas recrystallized

Sources & evidence

ORD record
ord-ae2d79c20a424a19a920bc9acc1c209f
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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