Sodium Hydroxide → 3'-Amino-4'-fluoroacetophenone

HRID 1476069Notes

Reaction equation

HRID 1476069 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[CH3:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([N+:18]([O-])=O)[CH:12]=1)=[O:10].[OH-].[Na+]>O.Cl>[CH3:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([NH2:18])[CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27346124'-Fluoro-3'-nitroacetophenoneHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 106069533'-Amino-4'-fluoroacetophenone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

At 0° C., a solution of 11.1 g (89 mmol) of tin chloride dihydrate in 12 ml of water was added dropwise over a period of 15 min to a solution of 3 g (16.4 mmol) of 4-fluoro-3-nitroacetophenone in 7.8 ml of 12 N hydrochloric acid. The reaction mixture was then heated at reflux for 15 min and subsequently stirred at RT overnight. The reaction mixture was then poured on ice, adjusted to pH 12 using 50% strength aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. This gave 2.47 g (purity 90%, 87% of theory) of the target compound.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 15 min
  3. additionThe reaction mixture was then poured on ice
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8588cf84e4114e258bdc88b71983ca6b
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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