Ethyl Acetate → HCID 19362527, compound

HRID 850256Notes

Reaction equation

HRID 850256 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=O)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][C:11]([O:16][CH3:17])=[CH:10][CH:9]=3.[Cl-].[OH:20][NH3+:21].C(OCC)(=O)C>C(O)C.O>[OH:20][N:21]=[C:7]1[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21645Hydroxylamine HClHCID 2579393,6-Dimethoxyfluoren-9-one

Product 1

HCID 19362527HCID 19362527, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.7 g (0.0195 mol) of 3,6-dimethoxyfluoren-9-one and 2.7 g (0.039 mol) of hydroxylammonium chloride are heated at 90° C. in a mixture of 50 ml of ethanol and 20 ml of water. After five hours the solution is poured into ice/water and ethyl acetate is added. The resulting suspension is filtered and the product that has been filtered off is washed with water and dried in vacuo. 4.25 g (86%) of 9-hydroxyimino-3,6-dimethoxyfluorene are obtained in the form of a yellow solid having a melting point of 230-240° C. According to 1H-NMR, that crude product still contains amounts of 3,6-dimethoxyfluoren-9-one. The crude product is, however, used in the subsequent step without being further purified and 3,6-dimethoxyfluoren-9-one is not removed until the end product is purified. Elemental analysis: C15H13NO3 (255.27)

Workup

  1. additionis added
  2. filtrationThe resulting suspension is filtered
  3. filtrationthe product that has been filtered off
  4. washis washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dc3f371c3ed34ab9860001ce60bd381d
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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