3-Methoxyacetophenone → HCID 131724469, compound

HRID 354251Notes

Reaction equation

HRID 354251 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=1.[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)=O.[OH-:25].[Na+].Cl.[NH2:28]O>COCCOC.O.CO>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([C:15](=[N:28][OH:25])[CH2:14][C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=2)[CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 114603-MethoxyacetophenoneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 131724469HCID 131724469, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A reaction vessel was charged with sodium hydride (as a 60% oil dispersion, 7.2 g, 180 mmol), DME (60 ml) and 2-chloro-5-trifluoromethylpyridine (10 g, 55.1 mmol). 3-Methoxyacetophenone (8.55 g, 56.9 mmol) in DME (20 ml) was added in portions to the mixture under nitrogen at room temperature. The mixture was stirred at ambient temperature for one hour then at 40-45° C. overnight. Upon the completion of the reaction, the mixture was cooled to 5° C. and 10% aqueous sodium hydroxide solution (30 ml) was slowly added to the reaction mixture followed by methanol (60 ml) then hydroxylamine hydrochloride (19.1 g, 357 mmol). The mixture was heated to 72° C. for 4 hours then cooled and diluted with water (2000 ml) with stirring. The resulting solid was removed by filtration and dried under vacuum. The crude solid was recrystallised from methanol to yield 7.6 g (44.4%) of the title compound.

Workup

  1. customat 40-45° C.
  2. customovernight
  3. customUpon the completion of the reaction
  4. temperaturethe mixture was cooled to 5° C.
  5. temperatureThe mixture was heated to 72° C. for 4 hours
  6. temperaturethen cooled
  7. stirringwith stirring
  8. customThe resulting solid was removed by filtration
  9. customdried under vacuum
  10. customThe crude solid was recrystallised from methanol

Sources & evidence

ORD record
ord-a7536ae944714184afc69138882320f7
Source dataset
uspto-grants-2004_06
Patent number
US06756498B2

Reaction notes

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