Ethanol → 1-[4-Fluoro-2-(methylamino)phenyl]ethanone

HRID 1089784Notes

Reaction equation

HRID 1089784 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9]S(C)=O)=[C:4]([NH:14][CH3:15])[CH:3]=1.C(O)C>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH3:9])=[C:4]([NH:14][CH3:15])[CH:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 10059700Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-

Product 1

HCID 199784601-[4-Fluoro-2-(methylamino)phenyl]ethanone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of 1-(4-fluoro-2-methylaminophenyl)-2-methylsulphinylethanone (161.0 g), prepared in a similar manner to that described in Example 1, in acetic acid (770 ml) was added to a stirred mixture of zinc dust (228.2 g), acetic acid (210 ml) and ethanol (392 ml) at 80° over 1 hour. The mixture was stirred at 80° for a further 2 hours and then allowed to cool to ambient temperature. The combined filtrates obtained after filtration and washing the residue with dichloromethane (400 ml) were concentrated by distillation until the temperature of the remaining mixture reached 132° and then cooled to ambient temperature. Water (1 1) and dichloromethane (330 ml) were added sequentially, the mixture stirred for 10 minutes and the layers then separated. The aqueous phase was extracted with further dichloromethane (2×200 ml), the organic extracts combined, then washed with aqueous sodium hydroxide solution (5M; 200 ml) and evaporated in vacuo. Distillation in vacuo (b.p. 74°, 0.4 mm Hg) of the residue gave 4'-fluoro-2'-(methylamino)acetophenone, m.p. 52°-53°.

Workup

  1. customThe combined filtrates obtained
  2. filtrationafter filtration
  3. washwashing the residue with dichloromethane (400 ml)
  4. concentrationwere concentrated by distillation until the temperature of the remaining mixture
  5. customreached 132°
  6. temperaturecooled to ambient temperature
  7. additionWater (1 1) and dichloromethane (330 ml) were added sequentially
  8. stirringthe mixture stirred for 10 minutes
  9. customthe layers then separated
  10. extractionThe aqueous phase was extracted with further dichloromethane (2×200 ml)
  11. washwashed with aqueous sodium hydroxide solution (5M; 200 ml)
  12. customevaporated in vacuo
  13. distillationDistillation in vacuo (b.p. 74°, 0.4 mm Hg) of the residue

Sources & evidence

ORD record
ord-0b7dd52346d84fbfb353cdf940ced869
Source dataset
uspto-grants-1992_01
Patent number
US05079264

Reaction notes

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