Hydroxylamine, O-ethyl- → HCID 136399315, compound

HRID 2164364Notes

Reaction equation

HRID 2164364 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][C:15](=[O:17])[C:14]([C:18](=O)[CH2:19][CH3:20])=[C:13]([OH:22])[CH2:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:23]([O:25][NH2:26])[CH3:24]>O1CCCC1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][C:15](=[O:17])[C:14]([C:18](=[N:26][O:25][CH2:23][CH3:24])[CH2:19][CH3:20])=[C:13]([OH:22])[CH2:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 69357Hydroxylamine, O-ethyl-HCID 178458867HCID 178458867, compound

Product 1

HCID 136399315HCID 136399315, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 10 ml of tetrahydrofuran was dissolved 2.0 g of 5-(4-acetamidophenyl)-2-propionyl-3-hydroxy-2-cyclohexen-1-one and to the solution was added 1.0 g of aqueous solution containing 50% of ethoxyamine. The mixture was kept for 15 hours at room temperature and it was poured into ice water and the crystal sedimented was collected with a filtering step. The crystal was dissolved in 20 ml of chloroform and the solution was washed with water and extracted with 15 ml of aqueous solution containing 5% of sodium hydroxide. To the alkaline solution was added a dilute hydrochloric acid solution and the crystal sedimented was extracted with chloroform. The solution was washed with water and dried with anhydrous magnesium sulfate and the chloroform was distilled off from it under reduced pressure. Thus 1.4 g of the desired compound was obtained. It was in the form of pale yellow crystals having a melting point of 135°-136° C.

Workup

  1. customthe crystal sedimented was collected with a filtering step
  2. dissolutionThe crystal was dissolved in 20 ml of chloroform
  3. washthe solution was washed with water
  4. extractionextracted with 15 ml of aqueous solution
  5. additioncontaining 5% of sodium hydroxide
  6. additionTo the alkaline solution was added a dilute hydrochloric acid solution
  7. extractionthe crystal sedimented was extracted with chloroform
  8. washThe solution was washed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. distillationthe chloroform was distilled off from it under reduced pressure

Sources & evidence

ORD record
ord-6a88e8ebe1be482890d60694de37306f
Source dataset
uspto-grants-1985_03
Patent number
US04504305

Reaction notes

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