Ethanol → 3-(alpha-Iminobenzyl)-4-hydroxy-6-phenyl-1-methyl-2(1H)-pyridinone

HRID 1706809Notes

Reaction equation

HRID 1706809 reaction equation
C[N:2]1[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]2[C:6](=[O:16])[NH:7][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][C:4]=2[O:3]1.[H][H].[CH2:26](O)C>[Pd]>[NH:2]=[C:17]([C:5]1[C:6](=[O:16])[N:7]([CH3:26])[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][C:4]=1[OH:3])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 20305026HCID 20305026, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1354009813-(alpha-Iminobenzyl)-4-hydroxy-6-phenyl-1-methyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 16.5 g. (0.0545 mole) of N-methyl-3,6-diphenyl-isoxazolo[4,5-c]pyridin-4(5H)-one, 330 ml. ethanol and 1.65 g. 10% palladium on carbon is hydrogenated at 50 psi and room temperature. The hydrogenation is ceased after 1 equivalent of hydrogen is absorbed (ca 2.5 hours). The mixture is treated with methylene chloride and the catalyst is removed by filtration. The solvents are removed in vacuo to a volume of ca 50 ml. and then ether is added, to precipitate solids which are removed by filtration to give 3-(α-iminobenzyl)-4-hydroxy-6-phenyl-1-methyl-2(1H)-pyridone, m.p. 238°-240° C. The above compound is dissolved in methanol and treated with sodium hydroxide solution to yield after evaporation the sodium salt of 3-(α-iminobenzyl)-4-hydroxy-6-phenyl-1-methyl-2(1H)-pyridone.

Workup

  1. additionA mixture of 16.5 g
  2. customis hydrogenated at 50 psi and room temperature
  3. customis absorbed (ca 2.5 hours)
  4. additionThe mixture is treated with methylene chloride
  5. customthe catalyst is removed by filtration
  6. customThe solvents are removed in vacuo to a volume of ca 50 ml
  7. additionand then ether is added
  8. customto precipitate solids which
  9. customare removed by filtration

Sources & evidence

ORD record
ord-f47736072faf4e31906e216669332937
Source dataset
uspto-grants-1980_06
Patent number
US04208532

Reaction notes

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