Water → HCID 86744481, compound

HRID 703570Notes

Reaction equation

HRID 703570 reaction equation
[Cl:1][C:2]12[C:9](=O)[CH2:8][CH:7]1[CH:6]=[CH:5][CH2:4][CH2:3]2.Cl.[NH2:12][OH:13].O>N1C=CC=CC=1>[Cl:1][C:2]12[C:9](=[N:12][OH:13])[CH2:8][CH:7]1[CH:6]=[CH:5][CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 22150666HCID 22150666, compound

Product 1

HCID 86744481HCID 86744481, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6.2 g of 6-chlorobicyclo[4.2.0]oct-2-en-7-one, prepared as shown in Preparation 7, and 3.4 g. of hydroxylamine hydrochloride in 30 ml of pyridine was stirred at 0° C. for 1 hour, then stirred overnight at room temperature. The mixture was poured into water and extracted with methylene chloride. The extract was washed with 0.5N hydrochloric acid followed by brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residual pyridine removed under high vacuum. The residue was dissolved in diethyl ether, filtered and solvent removed from the filtrate under reduced pressure, to give 6-chlorobicyclo[4.2.0]oct-2-en-7-one oxime, the compound of formula (6A) where Y is hydrogen, 5.4 g.

Workup

  1. customas shown in Preparation 7, and 3.4 g
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with 0.5N hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residual pyridine removed under high vacuum
  7. dissolutionThe residue was dissolved in diethyl ether
  8. filtrationfiltered
  9. customsolvent removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-7be6a3425b4c4f43a62b4426daee34bc
Source dataset
uspto-grants-1991_01
Patent number
US04983627

Reaction notes

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