Acetic Acid → Methyl 2-Amino-4-bromobenzoate

HRID 2191614Notes

Reaction equation

HRID 2191614 reaction equation
CO.C(O)(=O)C.[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([N+:18]([O-])=O)[CH:9]=1.C(=O)([O-])O.[Na+]>[Fe].C(OCC)(=O)C>[NH2:18][C:10]1[CH:9]=[C:8]([Br:7])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 18350461Methyl 4-bromo-2-nitrobenzoate

Product 1

HCID 17871390Methyl 2-Amino-4-bromobenzoateYield 56.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Iron powder 2.6 g was added to a mixed solution of methanol 20 mL and acetic acid 20 mL of methyl 4-bromo-2-nitrobenzoate 4.0 g, it was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added to it, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and solvent was removed under reduced pressure. Hexane was added to the obtained residue, solid matter was filtrated to give methyl 2-amino-4-bromobenzoate 2.0 g of white solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 3 hours
  3. filtrationwas filtrated
  4. customThe organic layer was separated
  5. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and solvent
  6. customwas removed under reduced pressure
  7. additionHexane was added to the obtained residue, solid matter
  8. filtrationwas filtrated

Sources & evidence

ORD record
ord-cd4fec8153614a74917febfd63d6807a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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