Hydroxyamine hydrochloride → 5-(5-Bromopyridin-3-yl)isoxazole

HRID 1620070Notes

Reaction equation

HRID 1620070 reaction equation
ON.Cl.[Br:4][C:5]1[CH:6]=[C:7]([C:11](=[O:17])[CH:12]=[CH:13][N:14](C)C)[CH:8]=[N:9][CH:10]=1>CO>[Br:4][C:5]1[CH:6]=[C:7]([C:11]2[O:17][N:14]=[CH:13][CH:12]=2)[CH:8]=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 670572791-(5-Bromopyridin-3-yl)-3-(dimethylamino)prop-2-ene-1-one

Product 1

HCID 680277295-(5-Bromopyridin-3-yl)isoxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxyamine•hydrochloride (42 mg) was added to a methanol (2 ml) solution containing 1-(5-bromopyridin-3-yl)-3-(dimethylamino)prop-2-ene-1-one obtained in the 1st step, followed by reflux for 2 hours. The solvent was distilled away under reduced pressure, and water was added to the obtained residue, followed by extraction with ethyl acetate. Then, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:3), and a white solid of 5-(5-bromopyridin-3-yl)isoxazole (59.5 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. temperatureby reflux for 2 hours
  3. distillationThe solvent was distilled away under reduced pressure, and water
  4. additionwas added to the obtained residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThen, the organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:3)

Sources & evidence

ORD record
ord-a4bb2d2ab04045f3887803fb1c7964c6
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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