Sodium Hydroxide → 1-(5-Amino-2-fluorophenyl)ethanone

HRID 323795Notes

Reaction equation

HRID 323795 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[F:13])=[O:3].O.O.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[F:13])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27810671-(2-Fluoro-5-nitrophenyl)ethan-1-oneHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 27811251-(5-Amino-2-fluorophenyl)ethanoneYield 48.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

25.4 g (152 mmol) of 2-fluoro-5-nitroacetophenone, 343 g (1.52 mol) of tin chloride dihydrate and 250 ml of ethyl acetate are introduced into a 1-liter three-necked flask. The reaction mixture is heated to 70° C. for 30 minutes and then poured onto 1 liter of crushed ice, 30% sodium hydroxide solution is added and the mixture is extracted with 3 times 350 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulphate and concentrated. 11.26 g of product are obtained in the form of an oil.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with 3 times 350 ml of ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-15568bd5eb5e4748b00b389d40bbaa98
Source dataset
uspto-grants-2001_04
Patent number
US06214882B1

Reaction notes

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