Tin dichloride dihydrate → 1-(4-Amino-3-fluorophenyl)pyridin-2-one

HRID 1434520Notes

Reaction equation

HRID 1434520 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.O.[Sn](Cl)Cl>C(O)C>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 589627441-(3-fluoro-4-nitro-phenyl)-1H-pyridin-2-one

Product 1

HCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.8 g (7.7 mmol) 1-(3-fluoro-4-nitro-phenyl)-1H-pyridin-2-one are dissolved in 360 ml of ethanol, combined with 8.7 g (38.4 mmol) tin(II)chloride-hydrate and refluxed for 45 min. The mixture is cooled and concentrated to dryness. The residue is combined with equal amounts of 1N sodium hydroxide solution and ethyl acetate. The precipitate is filtered off, water is added to the filtrate, the organic phase is separated off and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated to dryness.

Workup

  1. temperaturerefluxed for 45 min
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated to dryness
  4. filtrationThe precipitate is filtered off
  5. additionwater is added to the filtrate
  6. customthe organic phase is separated off
  7. extractionthe aqueous phase is extracted twice with ethyl acetate
  8. dry with materialThe combined organic phases are dried over sodium sulphate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-33f4cbfdb21d4875842935f46ce9ba22
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

Loading…