Hydrazine hydrate (1:1) → HCID 178506069, compound

HRID 877443Notes

Reaction equation

HRID 877443 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.O.[NH2:18][NH2:19]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:19][N:18]=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27714771-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 178506069HCID 178506069, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of compound 34 (15.0 g, 50.0 mmol) and hydrazine hydrate (10.0 g, 56 mmol) in methanol 150 mL was heated to reflux for 1 h. After cooling in an ice bath for 10 min, the solvent was removed, water (100 mL) added, and the reaction mixture extracted with ethyl acetate (50 mL×3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated crude. The crude product was purified by column chromatography using 10% ethyl acetate in hexane, to afford the crude pyrazole intermediate 34a.

Workup

  1. temperatureto reflux for 1 h
  2. temperatureAfter cooling in an ice bath for 10 min
  3. customthe solvent was removed
  4. additionwater (100 mL) added
  5. extractionthe reaction mixture extracted with ethyl acetate (50 mL×3)
  6. washCombined organic layer was washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated crude
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e6f474de374f43ca82e50b7adc2a5e20
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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