Hydroxyamine hydrochloride → HCID 86107496, compound

HRID 544617Notes

Reaction equation

HRID 544617 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[O:21][N:20]=[C:19]([CH3:22])[CH:18]=2)=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>C(O)C.O>[C:1](=[N:26][OH:27])([C:5]1[CH:24]=[CH:23][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[O:21][N:20]=[C:19]([CH3:22])[CH:18]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5271198HCID 5271198, compound

Product 1

HCID 86107496HCID 86107496, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.6 g of 5-[7-(4-propionylphenoxy)heptyl]-3-methylisoxazole (Example 32) in 40 ml of ethanol was added a solution of 368 mg of hydroxylamine hydrochloride and 730 mg of sodium acetate in 8 ml of water. The reaction mixture was heated at reflux overnight and then concentrated in vacuo. The residue was recrystallized from aqueous ethanol to give 1.0 g of 5-[7-(4-propionylphenoxy)heptyl]-3-methylisoxazole oxime, colorless solid, m.p. 88°-89° C.; MIC vs. rhinovirus Type 2 in vitro=2.6 μg/ml; and vs. polio-2 virus at 0.2 μg/ml.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-8d27d05bab414cb6bceb9441e3b9d8d6
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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