Pyridine → HCID 22554941, compound

HRID 985114Notes

Reaction equation

HRID 985114 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:29])[CH:10]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=O)=[CH:5][CH:4]=1.Cl.NO.[N:33]1C=CC=CC=1>C(O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:10]2[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[N:33][O:29][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 22554791HCID 22554791, compound

Product 1

HCID 22554941HCID 22554941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the 1,3-diketone obtained in step 3 (1.0 equiv.), hydroxylamine hydrochloride (1.5 equiv.), pyridine (2.0 equiv.) and ethanol was heated to reflux overnight. Cooled to rt and removed solvent in vacuo. Water and ethyl acetate were added. The organic layer was separated, washed with dil. HCl, brine, dried, filtered and the solvent was concentrated in vacuo. The product 1-[4,5-bis(4-methoxyphenyl)isoxazol-3-yl]-4-methoxybenzene was obtained as an off white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customremoved solvent in vacuo
  4. additionWater and ethyl acetate were added
  5. customThe organic layer was separated
  6. washwashed with dil. HCl, brine
  7. customdried
  8. filtrationfiltered
  9. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-3fa417b84c09449f88f8882be73250f3
Source dataset
uspto-grants-2005_03
Patent number
US06869969B2

Reaction notes

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