Hydroxyamine hydrochloride → HCID 86738976, compound

HRID 434710Notes

Reaction equation

HRID 434710 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[C:7](=[CH2:17])[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=O)[CH2:11][C:5]=2[CH:4]=1.Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[C:7](=[CH2:17])[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[N:21][OH:22])[CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 13194190HCID 13194190, compound

Product 1

HCID 86738976HCID 86738976, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methoxy-5-methylene-10-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (9.7 g, 0.0388 mol), hydroxylamine hydrochloride (3.42 g, 0.0492 mol), and sodium acetate (4.26 g, 0.0519 mol) in methanol (194 ml) is heated under reflux for 2 hours. The solvent is removed under reduced pressure, the residue is slurried in water (200 ml), the pH is adjusted to 8 with concentrated aqueous ammonia, and the slurry is extracted with ether (3×105 ml). The combined extracts are dried over MgSO4 and filtered, and the filtrate is evaporated to yield 10.1 g (98%) of crude material. A sample recrystallized from ether has m.p. 125°-127° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solvent is removed under reduced pressure
  3. extractionthe slurry is extracted with ether (3×105 ml)
  4. dry with materialThe combined extracts are dried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-e7632a350cce45d5ba5ed1e233903fa7
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

Loading…