3-phenyl-5-(beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide → HCID 178485723, compound

HRID 1439518Notes

Reaction equation

HRID 1439518 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH2:16][CH:17]([OH:24])[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.[H][H]>[Pd].C(O)C>[NH2:8][C:7](=[C:11]([C:10](=[O:9])[CH2:16][CH:17]([OH:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]([NH:14][CH3:15])=[O:13])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 203050053-phenyl-5-(beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 178485723HCID 178485723, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 30.0 grams (0.093 mole) of 3-phenyl-5-(β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide, 600 milliliters of ethanol and 3.0 grams of 10 percent Palladium on carbon in hydrogenated at 50 p.s.i. until 1 equivalent of hydrogen is absorbed (about 5 hours). The mixture is filtered and the filtrate evaporated in vacuo. The residue is then crystallized from methylene chloride petroleum ether to give 2-(α-aminobenzylidene)-5-hydroxy-N-methyl-3-oxo-5-phenylvaleramide, m.p. 72° C. - 76° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue is then crystallized from methylene chloride petroleum ether

Sources & evidence

ORD record
ord-fc0ddebd4d1f4bb7b13629b9617acdb0
Source dataset
uspto-grants-1977_11
Patent number
US04060533

Reaction notes

Loading…