Hydroxyamine hydrochloride → HCID 68027729, compound

HRID 340463Notes

Reaction equation

HRID 340463 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 68027729HCID 68027729, compound

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-98d9d2fd95844bd7b0cae9832d4dbbf0
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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