Pyridine → HCID 22554941, compound

HRID 351910Notes

Reaction equation

HRID 351910 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 was 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-9c245e0f18614e63b4aa412b85639ddc
Source dataset
uspto-grants-2004_06
Patent number
US06743815B2

Reaction notes

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