Hydroxyamine hydrochloride → 5,7-dimethyl-8-methoxy-9-hydroxyiminomethyl-1,2,3,4-tetrahydro-9H-fluorene

HRID 2051433Notes

Reaction equation

HRID 2051433 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1[CH:17]=[C:16]([CH3:18])[C:15]([O:19][CH3:20])=[C:14]2[C:6]=1[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=1[CH:13]2[CH2:21]C=O>C(O)C.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH3:4][C:5]1[CH:17]=[C:16]([CH3:18])[C:15]([O:19][CH3:20])=[C:14]2[C:6]=1[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=1[CH:13]2[CH:21]=[N:2][OH:3]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 151572015,7-dimethyl-8-methoxy-9-formylmethyl-1,2,3,4-tetrahydro-9H-fluorene

Product 1

HCID 867447975,7-dimethyl-8-methoxy-9-hydroxyiminomethyl-1,2,3,4-tetrahydro-9H-fluorene

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21889567Chloroform ethanolSolvent2×

Procedure

500 Milligrams of hydroxylamine hydrochloride was added to an ethanol-chloroform (5:1) solution containing 910 mg of 5,7-dimethyl-8-methoxy-9-formylmethyl-1,2,3,4-tetrahydro-9H-fluorene in 18 ml of ethanol-chloroform and the mixture was refluxed with heating for 2 hours. The reaction mixture was diluted with chloroform and then washed with saturated aqueous sodium chloride solution and subsequently the solvent was distilled off. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10) to obtain 670 mg of 5,7-dimethyl-8-methoxy-9-hydroxyiminomethyl-1,2,3,4-tetrahydro-9H-fluorene

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. washwashed with saturated aqueous sodium chloride solution
  4. distillationsubsequently the solvent was distilled off
  5. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-994356ec970a4667990c64fce61e76fd
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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