Hydrochloric Acid → 1-(3-Amino-5-bromo-2-methoxy-phenyl)-ethanone

HRID 1295966Notes

Reaction equation

HRID 1295966 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.Cl>[Fe].CO>[NH2:13][C:4]1[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 229296971-(5-Bromo-2-methoxy-3-nitrophenyl)ethan-1-one

Product 1

HCID 229296751-(3-Amino-5-bromo-2-methoxy-phenyl)-ethanoneYield 88.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Iron (15 g) was added to a mixture of the 1-(5-bromo-2-methoxy-3-nitrophenyl)-1-ethanone (16.2 g), concentrated hydrochloric acid (20 mL) and methanol (60 mL) at room temperature. After stirring the mixture at 60° C. for 1 hour, it was neutralized with saturated aqueous sodium hydrogencarbonate and extraction was performed with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (12.8 g) as a yellow oil.

Workup

  1. extractionit was neutralized with saturated aqueous sodium hydrogencarbonate and extraction
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1ca9d0251cfe4df6a39456c7d46545e3
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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