Hydroxylamine sulfate → HCID 22462506, compound

HRID 1936980Notes

Reaction equation

HRID 1936980 reaction equation
[CH3:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]2[C:6](=[O:14])[CH:7]3[CH2:13][CH2:12][CH2:11][CH:8]3[C:9]=2[CH:10]=1.S([O-])([O-])(=O)=O.O[NH3+:24].O[NH3+].C([O-])(=O)C.[Na+]>C1COCC1.C(O)C.O>[CH3:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]2[NH:24][C:6](=[O:14])[CH:7]3[CH2:13][CH2:12][CH2:11][CH:8]3[C:9]=2[CH:10]=1.[N+:15]([C:3]1[CH:2]=[CH:10][C:9]2[CH:8]3[CH2:11][CH2:12][CH2:13][CH:7]3[C:6](=[O:14])[NH:24][C:5]=2[CH:4]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 24846Hydroxylamine sulfateHCID 517045Sodium AcetateHCID 22462494HCID 22462494, compound

Product 1

HCID 22462506HCID 22462506, compound

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

The mixture that consists of 6-nitro-2,3,3a,8a-tetrahydro-1H-cyclopentta]inden-8-one and 5-methyl-6-nitro-2,3,3a,8a-tetrahydro-1H-cyclopent[a]inden-8-one (3.76 g) is dissolved with hydroxylammonium sulfate (5.58 g, 34 mmol) and sodium acetate (9.25 g, 68 mmol) in THF-ethanol-water 1:1:1 (180 ml). The batch is stirred for 6 hours at 60° C., left for three days at room temperature, concentrated by evaporation, diluted with ether, washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is purified on silica gel with the eluant ether-hexane. Yield: 3.76 g; the oxime mixture is dissolved at 120° C. in polyphosphoric acid. The batch is stirred for four hours at 120° C., it is poured onto ice water after cooling and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is prepurified on silica gel with ethyl acetate-hexane, and the mixture is then separated using preparative HPLC (LC.50 Novapak column, eluant: methanol-aqueous ammonium acetate solution):

Workup

  1. waitleft for three days at room temperature
  2. concentrationconcentrated by evaporation
  3. additiondiluted with ether
  4. washwashed with saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue is purified on silica gel with the eluant ether-hexane
  8. dissolutionthe oxime mixture is dissolved at 120° C. in polyphosphoric acid
  9. stirringThe batch is stirred for four hours at 120° C.
  10. additionit is poured onto ice water
  11. temperatureafter cooling
  12. extractionextracted with ethyl acetate
  13. dry with materialThe combined extracts are dried (Na2SO4)
  14. concentrationconcentrated by evaporation in a vacuum
  15. customthe mixture is then separated

Sources & evidence

ORD record
ord-5cb4225eb7fd4140acb679acbfdbd3dd
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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