Hydroxyamine hydrochloride → HCID 21414236, compound

HRID 436372Notes

Reaction equation

HRID 436372 reaction equation
[CH2:1]1[CH:8]2[CH:2]1[C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[C:5](=O)[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=12.Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[CH2:1]1[CH:8]2[CH:2]1[C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[C:5](=[N:19][OH:20])[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=12

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18667964HCID 18667964, compound

Product 1

HCID 21414236HCID 21414236, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6.6 g (0.03 mole) of 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one, 8.4 g (0.12 mole) of hydroxylamine hydrochloride in 120 ml of pyridine was held at reflux for 18.5 hrs. The solvent was evaporated 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, and saturated brine, dried and solvent evaporated to give 7.4 g of crude 1,a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one oxime, mp 201° (ex. MeOH, dried at 110°/0.1 mm). The NMR spectrum in CDCl3 -DMSO-d6 : a singlet at δ10.9 (1H), multiplet at 6.9-7.6 (8H), multiplet at 2.1-2.6 (2H) and multiplet at 1.3-1.8 (2H). Anal. Calcd. for C16H13NO: C, 81.46; H, 5.57; N, 5.95. Found: C, 81.48; H, 5.68; N, 6.08. Mass spec.: Calcd. for C16H13NO: 235.0996. Found: 235.0997.

Workup

  1. temperatureat reflux for 18.5 hrs
  2. customThe solvent was evaporated 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, and saturated brine
  6. customdried
  7. customsolvent evaporated
  8. customto give
  9. dry with material7.4 g of crude 1,a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one oxime, mp 201° (ex. MeOH, dried at 110°/0.1 mm)

Sources & evidence

ORD record
ord-23d4d52e00c44db58e2d8a688a4f591b
Source dataset
uspto-grants-1977_02
Patent number
US04008331

Reaction notes

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