Pyridine → HCID 22554941, compound

HRID 1935590Notes

Reaction equation

HRID 1935590 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 in rt and removed solvent in vacuo. Water and ethyl acetate were added. The organic layer was separated, washed with dil. HCl, lurine, 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 while 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, lurine
  7. customdried
  8. filtrationfiltered
  9. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-94680461394344638b65ff5c080578ce
Source dataset
uspto-grants-2002_05
Patent number
US06387920B2

Reaction notes

Loading…