Hydrazine hydrate (1:1) → HCID 18704553, compound

HRID 2287318Notes

Reaction equation

HRID 2287318 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([C:12](=O)[CH2:13][C:14](=O)[CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[C:4]([F:24])[CH:3]=1.O.[NH2:26][NH2:27]>C(O)C>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([C:12]2[CH:13]=[C:14]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[NH:27][N:26]=2)=[C:4]([F:24])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18704565HCID 18704565, compound

Product 1

HCID 18704553HCID 18704553, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 1-(4-chloro-2-fluoro-5-isopropoxy-phenyl)-4,4-diethoxybutane-1,3-dione (Example H7) is initially introduced into 150 ml of dry ethanol. 2.90 g of hydrazine monohydrate are added dropwise at room temperature, while stirring. The mixture is then stirred for 4 hours, while heating under gentle reflux, and is subsequently cooled and the alcohol is removed on a rotary evaporator in vacuo. The residue obtained is partitioned between aqueous sodium bicarbonate solution and ethyl acetate. After extraction by shaking and separation of the phases, the organic phase is washed with water and then dried over sodium sulfate and concentrated. 17.5 g of a dark yellow oil are obtained.

Workup

  1. stirringThe mixture is then stirred for 4 hours
  2. temperaturewhile heating under gentle reflux
  3. temperatureis subsequently cooled
  4. customthe alcohol is removed on a rotary evaporator in vacuo
  5. customThe residue obtained
  6. customis partitioned between aqueous sodium bicarbonate solution and ethyl acetate
  7. extractionAfter extraction
  8. stirringby shaking
  9. customseparation of the phases
  10. washthe organic phase is washed with water
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-16bbff89a2d7498aaf1d4b8f907b6bc1
Source dataset
uspto-grants-2000_07
Patent number
US06083881

Reaction notes

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