Potassium Hydroxide → HCID 12889668, compound

HRID 894329Notes

Reaction equation

HRID 894329 reaction equation
COC([NH:5][CH2:6][CH:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)=O.[OH-].[K+]>Cl>[NH2:5][CH2:6][CH:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12889667HCID 12889667, compound

Product 1

HCID 12889668HCID 12889668, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A 5 g. portion of the product of Example 32 was slurried in 50 percent aqueous hydrochloric acid and refluxed overnight. The mixture was then cooled and neutralized with potassium hydroxide, and extracted with chloroform. The chloroform layer was concentrated to 10 ml., and eluted through a 12-meter column of polystyrene gel beads with chloroform as the eluting solvent. The desired product was the second fraction off the column. The yield was 2 g. of 5-aminomethyl-3-phenyl-2-isoxazoline, an oily liquid, NMR multiplets at 2.57-3.83, 4.43-4.97, 7.08-7.60 and 7.42-7.80 ppm., and a singlet at 1.38 ppm.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was then cooled
  3. extractionextracted with chloroform
  4. concentrationThe chloroform layer was concentrated to 10 ml
  5. wash, and eluted through a 12-meter column of polystyrene gel

Sources & evidence

ORD record
ord-d3e2882ac2e14ff1ae3256fd435816a5
Source dataset
uspto-grants-1981_08
Patent number
US04283403

Reaction notes

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