Hydroxyamine hydrochloride → HCID 21414236, compound

HRID 1657529Notes

Reaction equation

HRID 1657529 reaction equation
CO[C:3]1(OC)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]2[CH2:14][CH:6]2[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.Cl.[NH2:22][OH:23]>N1C=CC=CC=1>[CH2:14]1[CH:7]2[CH:6]1[C:5]1[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=1[C:3](=[N:22][OH:23])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=12

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21414232HCID 21414232, compound

Product 1

HCID 21414236HCID 21414236, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.5 g (5.6 moles) of 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one dimethylketal, 2.5 g of hydroxylamine hydrochloride in 20 ml of pyridine was held at reflux for 18 hr. The solvent was removed under reduced pressure and the residue was dissolved with a mixture of water and methylene chloride. The layers were separated and the organic layer was in turn washed with 10% hydrochloric acid, saturated sodium bicarbonate solution and saturated brine, dried and solvent removed to give 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one oxime. All of the physical properties were identical to those obtained by Example 1A. Note: The oxime forms a solvate with methanol.

Workup

  1. temperatureat reflux for 18 hr
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved with a mixture of water and methylene chloride
  4. customThe layers were separated
  5. washwashed with 10% hydrochloric acid, saturated sodium bicarbonate solution and saturated brine
  6. customdried
  7. customsolvent removed

Sources & evidence

ORD record
ord-3bb6c56df7ef47658adf7d9c1e2a2ef9
Source dataset
uspto-grants-1976_06
Patent number
US03960956

Reaction notes

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