Water → HCID 135929566, compound

HRID 1678704Notes

Reaction equation

HRID 1678704 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].Cl.Cl.[CH2:8]([NH:15][NH2:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C1(C)C(C)=CC=CC=1>[CH2:8]([N:15]1[C:8]2[C:9](=[CH:10][CH:11]=[C:1]([OH:4])[CH:2]=2)[C:14]([CH2:13][CH3:12])=[N:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 146540Benzylhydrazine dihydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 135929566HCID 135929566, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1-(2-Fluoro-4-hydroxyphenyl)propan-1-one (5.37 g) that can be produced by the method described in Reference Example 9 or the like, sodium acetate (12.75 g; manufactured by Wako Pure Chemical Industries, Ltd.) and benzylhydrazine dihydrochioride (9.452 g; manufactured by Sigma-Aldrich Co.) were suspended in xylene (76 mL). The suspension was stirred overnight at reflux using a Dean-Stark apparatus. The reaction solution was cooled to room temperature, subsequently water was added thereto, and the mixture was extracted two times with ethyl acetate. The organic layer was washed two times with water and with brine, and was dried over anhydrous sodium sulfate. Subsequently, the solvent was evaporated under reduced pressure. Before completely evaporating the solvent, precipitates were filtered, and the solids were washed with n-hexane. Thus, the title compound (4.76 g) was obtained. Furthermore, the filtrate was concentrated under reduced pressure, and the solids precipitating in the middle of the concentrating process were also filtered. Thus, the title compound (3.44 g) was obtained.

Workup

  1. temperatureat reflux
  2. extractionthe mixture was extracted two times with ethyl acetate
  3. washThe organic layer was washed two times with water
  4. dry with materialwith brine, and was dried over anhydrous sodium sulfate
  5. customSubsequently, the solvent was evaporated under reduced pressure
  6. customBefore completely evaporating the solvent
  7. customprecipitates
  8. filtrationwere filtered
  9. washthe solids were washed with n-hexane

Sources & evidence

ORD record
ord-42eaf887a06446729e5cc4da257d508c
Source dataset
uspto-grants-2011_08
Patent number
US08008506B2

Reaction notes

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