5-methyl-6,7-dihydro-3,6-diphenyl isoxazolo[4,5-c]pyridin-4(5H)-one → 3-alpha-iminobenzyl-5,6-dihydro-4-hydroxy-1-methyl-6-phenyl-2(1H)-pyridone

HRID 1701183Notes

Reaction equation

HRID 1701183 reaction equation
[CH3:1][N:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][C:5]2[O:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:3]1=[O:23].[H][H]>[Pd].C(O)C>[NH:15]=[C:16]([C:4]1[C:3](=[O:23])[N:2]([CH3:1])[CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][C:5]=1[OH:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 203488365-methyl-6,7-dihydro-3,6-diphenyl isoxazolo[4,5-c]pyridin-4(5H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1357653603-alpha-iminobenzyl-5,6-dihydro-4-hydroxy-1-methyl-6-phenyl-2(1H)-pyridone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4 grams (0.013 mole) of 5-methyl-6,7-dihydro-3,6-diphenyl isoxazolo[4,5-c]pyridin-4(5H)-one, 0.44 grams palladium on carbon and 80 ml. ethanol is hydrogenated at 50 psi until the equivalent amount of hydrogen is absorbed. The catalyst is filtered and washed thoroughly with ethanol. The ethanol is evaporated in vacuo and the residue recrystallized to give 3-α-iminobenzyl-5,6-dihydro-4-hydroxy-1-methyl-6-phenyl-2(1H)-pyridone; m.p. 117° to 120° C.

Workup

  1. customis absorbed
  2. filtrationThe catalyst is filtered
  3. washwashed thoroughly with ethanol
  4. customThe ethanol is evaporated in vacuo
  5. customthe residue recrystallized

Sources & evidence

ORD record
ord-833cb3f514d04b85881e6463550090a3
Source dataset
uspto-grants-1980_03
Patent number
US04191827

Reaction notes

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