3-phenyl-5-(beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide → 5-methyl-6,7-dihydro-3,6-diphenyl isoxazolo[4,5-c]pyridin-4(5H)-one

HRID 66308Notes

Reaction equation

HRID 66308 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH2:16][CH:17](O)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O>[CH3:15][N:14]1[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]=2[C:12]1=[O:13]

Participants

3

Reactant 1

HCID 203050053-phenyl-5-(beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 550 ml. of polyphosphoric acid maintained at a temperature of 100° to 105° C. there is added 36.5 grams (0.114 moles) 3-phenyl-5-(β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide in portions. The mixture is then stirred at 100° for 5 hours and then poured onto 2 liters of ice and water. The resulting solid is filtered and purified by recrystallization to give 5-methyl-6,7-dihydro-3,6-diphenyl isoxazolo[4,5-c]pyridin-4-(5H)-one; m.p. 108° to 111° C.

Workup

  1. filtrationThe resulting solid is filtered
  2. custompurified by recrystallization

Sources & evidence

ORD record
ord-c5ee9a1dcff54d39a4d6c74bb1f1734f
Source dataset
uspto-grants-1978_12
Patent number
US04131679

Reaction notes

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