Hydrochloric Acid → HCID 69097053, compound

HRID 2409951Notes

Reaction equation

HRID 2409951 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].Br[CH2:12][C:13](=O)[C:14]([CH3:17])([CH3:16])[CH3:15].Cl.O>C(O)C>[C:14]([C:13]1[NH:6][C:5]2[C:7]([CH:12]=1)=[CH:8][C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=2)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21642BromopinacoloneHCID 131036924-Chloro-3-methoxyaniline

Product 1

HCID 69097053HCID 69097053, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-3-methoxyaniline (4.68 g) in ethanol (4.5 mL) was heated under reflux while stirring. To the solution was added 1-bromo-3,3-dimethyl-2-butanone (0.243 mL×5) in five portions at an interval of 5 minutes, and this mixture was heated under reflux while stirring for 4 hours. The reaction mixture was left to be cooled. To the reaction mixture were added 2 mol/L hydrochloric acid and water successively, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium 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 (893 mg). 1H-NMR (CDCl3) δ ppm: 1.37 (9H, s), 3.89 (3H, s), 6.09-6.16 (1H, m), 6.88 (1H, s), 7.50 (1H, s), 7.72-8.12 (1H, br).

Workup

  1. temperatureunder reflux
  2. temperaturethis mixture was heated
  3. temperatureunder reflux
  4. stirringwhile stirring for 4 hours
  5. waitThe reaction mixture was left
  6. temperatureto be cooled
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried over anhydrous magnesium 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-2fe82a2845e84d5e99d6f42e5db56e05
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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