Hydrochloric Acid → HCID 15728477, compound

HRID 1463374Notes

Reaction equation

HRID 1463374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8](O)[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Sn].Cl.C(=O)([O-])[O-].[K+].[K+]>S([O-])([O-])(=O)=O.[Cu+2].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH3:18])[CH3:19])=[CH:15][CH:16]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5352426Tin atomHCID 157284762-(3-Chlorophenyl)-2-hydroxy-1-[4-(dimethylamino)phenyl]ethanone

Product 1

HCID 15728477HCID 15728477, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 9.08 g, of 2-(3-chlorophenyl)-2-hydroxy-1-[4-(dimethylamino)phenyl]ethanone, 3 equivalents of mossy tin, a spatula tip of copper (II) sulfate, 20 ml of concentrated HCl, and 60 ml of 95% ethanol was stirred at reflux 3 hours. The mixture was basified with potassium carbonate solution and filtered. The cake was washed with ethyl acetate and the filtrate separated. The aqueous phase was extracted with ethyl acetate and the combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (10:1 hexane-ethyl acetate) and then recrystallized from ethyl acetate-hexane to give 3.8 g of 2-(3-chlorophenyl)-1-[4-(dimethylamino)phenyl]ethanone, m.p. 126°-128° C.

Workup

  1. additionA mixture of 9.08 g
  2. temperatureat reflux 3 hours
  3. filtrationfiltered
  4. washThe cake was washed with ethyl acetate
  5. customthe filtrate separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. dry with materialthe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (10:1 hexane-ethyl acetate)
  11. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-06e4f9a2787e438fb0d27ef4bb4595f6
Source dataset
uspto-grants-1994_04
Patent number
US05300527

Reaction notes

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