Hydrochloric Acid → HCID 86703326, compound

HRID 2410011Notes

Reaction equation

HRID 2410011 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[CH3:10])[NH2:6].Br[CH2:12][C:13]([C:15]1([CH3:18])[CH2:17][CH2:16]1)=O.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:7]([CH:12]=[C:13]([C:15]3([CH3:18])[CH2:17][CH2:16]3)[NH:6]2)=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 278823-Methoxy-4-methylanilineHCID 128223082-Bromo-1-(1-methylcyclopropyl)ethan-1-one

Product 1

HCID 86703326HCID 86703326, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3-methoxy-4-methylaniline (2.26 g) in ethanol (7 mL) was heated under reflux while stirring. To the solution was added slowly a solution of 2-bromo-1-(1-methylcyclopropyl)ethan-1-one (885 mg) in ethanol (3 mL), and this mixture was heated under reflux for 3 hours while stirring. The reaction mixture was left to be cooled. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (588 mg).

Workup

  1. temperatureunder reflux
  2. temperaturethis mixture was heated
  3. temperatureunder reflux for 3 hours
  4. stirringwhile stirring
  5. waitThe reaction mixture was left
  6. temperatureto be cooled
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with 1 mol/L hydrochloric acid
  9. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0dc455ee163c456b927f05dbf4691630
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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