Hydroxyamine hydrochloride → 10-hydroxyimino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 434700Notes

Reaction equation

HRID 434700 reaction equation
[CH2:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][C:5](=O)[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>CO>[OH:20][N:19]=[C:5]1[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]=2[C:2](=[CH2:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 1201705HCID 1201705, compound

Product 1

HCID 82670410-hydroxyimino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 16.5 g of the oxo-compound from Step C, 6.6 g of hydroxylamine hydrochloride, 8.2 of sodium acetate and 300 ml of methanol was heated under reflux for 5 hours. The solvent was evaporated and the residue was treated with 250 ml of water. The mixture was extracted with 3×150 ml of ether, and the extract was dried, filtered, and evaporated to give 16.8 g of 10-hydroxyimino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene, m.p. 156°-160° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was evaporated
  4. additionthe residue was treated with 250 ml of water
  5. extractionThe mixture was extracted with 3×150 ml of ether
  6. customthe extract was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9fb3f891f46a4894a13d4a79f0a9b96f
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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