Hydroxyamine hydrochloride → HCID 86739741, compound

HRID 1633332Notes

Reaction equation

HRID 1633332 reaction equation
[CH2:1]([N:8]1[C@H:17]2[C@@H:12]([CH2:13][CH2:14][C:15](=O)[CH2:16]2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21]>C(O)C.N1C=CC=CC=1>[CH2:1]([N:8]1[C@H:17]2[C@@H:12]([CH2:13][CH2:14][C:15](=[N:20][OH:21])[CH2:16]2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 71369429(4aR,8aR)-1-Benzyloctahydroquinolin-7(1H)-one

Product 1

HCID 86739741HCID 86739741, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

To (±)-1-benzyl-trans-decahydro-7-quinolinone (D.11) (1.17 g), dissolved in ethanol (20 ml) and pyridine (0.8 ml), was added hydroxylamine hydrochloride (0.4 g), and the mixture was heated under reflux for 1 hr. On cooling, the ethanol was removed under reduced pressure and the residue was treated with dilute potassium carbonate solution. The product was extracted with chloroform and dried (K2CO3). Removal of the solvent afforded crude (±)-1-benzyl-trans-decahydro-7-quinolinone oxime (D.12) (1.1. g, ca 88%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureOn cooling
  4. customthe ethanol was removed under reduced pressure
  5. additionthe residue was treated with dilute potassium carbonate solution
  6. extractionThe product was extracted with chloroform
  7. dry with materialdried (K2CO3)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-0db8048f425b4b9bb1823d8d8740e311
Source dataset
uspto-grants-1984_10
Patent number
US04480099

Reaction notes

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