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

HRID 861087Notes

Reaction equation

HRID 861087 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]([Cl:13])=[CH:9][CH:8]=1)=[O:6].Cl.NO>C(O)C>[Cl: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 540776133-Dimethylamino-1-(4-chlorophenyl)-2-(pyridin-4-yl)-2-propen-1-one

Product 1

HCID 220374565-(4-Chlorophenyl)-4-(pyridin-4-yl)isoxazoleYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylamino-1-(4-chlorophenyl)-2-(pyridin-4-yl)-2-propen-1-one (22.80 g, 79.7 mmol), hydroxylamine hydrochloride (18.01 g, 0.26 mole), and 150 mL ethanol was heated to reflux for 30 minutes. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was dissolved in 1N hydrochloric acid and then treated with an aqueous saturated solution of sodium bicarbonate. The precipitates were collected by filtration, washed with water and ethanol, and dried to yield 5-(4-chlorophenyl)-4-(pyridin-4-yl)isoxazole (20.50 g, 93%). m.p. 120.8–120.9° C. 1H NMR (CDCl3/CD3OD/300 MHz) δ 8.53 (d, 2H), 8.46(s, 1H), 7.51(d, 2H), 7.41–7.34 (m, 4H). ESLRMS m/z 257 (M+H). ESHRMS m/z 257.0457 (M+H, C14H9N2OCl requires 257.0482).

Workup

  1. temperatureto reflux for 30 minutes
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 1N hydrochloric acid
  4. additiontreated with an aqueous saturated solution of sodium bicarbonate
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water and ethanol
  7. customdried

Sources & evidence

ORD record
ord-a9589658fe8145e1892eba87fed6d276
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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