Hydrochloric Acid → (2-Amino-4,5-dimethoxy-phenyl)-(3-bromo-phenyl)-methanone

HRID 1191329Notes

Reaction equation

HRID 1191329 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=2[NH:20]C(=O)C(C)(C)C)=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[NH2:20][C:11]1[CH:12]=[C:13]([O:18][CH3:19])[C:14]([O:16][CH3:17])=[CH:15][C:10]=1[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66849003N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2,2-dimethylpropanamide

Product 1

HCID 7148514(2-Amino-4,5-dimethoxy-phenyl)-(3-bromo-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2,2-dimethylpropanamide (7.9 g, 18.9 mmol) in 1,4-dioxane (80 mL) was added concentrated HCl (9.55 g, 94.2 mmol). The mixture was refluxed for 2 hours. After cooling to room temperature, 1,4-dioxane was removed in vacuum and the residue was diluted with water (100 mL) and EtOAc (100 mL), then neutralized with NaHCO3 to pH=8. The mixture was extracted with EtOAc (80 mL×3). The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated under vacuum to afford (2-amino-4,5-dimethoxyphenyl)(3-bromophenyl)methanone. MS (M+H)=336 and 338.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. custom1,4-dioxane was removed in vacuum
  3. additionthe residue was diluted with water (100 mL) and EtOAc (100 mL)
  4. extractionThe mixture was extracted with EtOAc (80 mL×3)
  5. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-21e84717c3e54a3bbdd99859834e2267
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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