Hydroxyamine hydrochloride → 5-(4-Fluorophenyl)-4-(pyridin-4-yl)isoxazole

HRID 54933Notes

Reaction equation

HRID 54933 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].Cl.NO>C(O)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[O:6][N:2]=[CH:3][C:4]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 545188383-(Dimethylamino)-1-(4-fluorophenyl)-2-(pyridin-4-yl)prop-2-en-1-one

Product 1

HCID 229090125-(4-Fluorophenyl)-4-(pyridin-4-yl)isoxazoleYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(4-fluorophenyl)-2-(pyridin-4-yl)-2-propen-1-one (6.15 g) and hydroxylamine hydrochloride (4.75 g) in dry ethanol (40 ml) was refluxed for 20 minutes. The mixture was cooled and concentrated in vacuo. The residue was dissolved in dilute hydrochloric acid and then treated with an aqueous saturated sodium bicarbonate solution. The precipitates were collected by filtration, washed with water, and dried to give 5-(4-fluorophenyl)-4-(pyridin-4-yl)isoxazole (5.35 g).

Workup

  1. temperaturewas refluxed for 20 minutes
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dilute hydrochloric acid
  5. additiontreated with an aqueous saturated sodium bicarbonate solution
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f51bbb16e8df4fcfbfdb14dd1bc794e6
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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