Acetic Acid → Methyl 2-Amino-4-bromobenzoate

HRID 1673331Notes

Reaction equation

HRID 1673331 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-bromobenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.6 g of iron powder was added to a mixed solution of 20 mL of methanol and 20 ml, of acetic acid containing 4.0 g of methyl 4-bromo-2-nitrobenzoate, and the resulting mixture was heated to reflux for 3 hours. After the reaction mixture was cooled to room temperature, a saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue and a solid substance was separated by filtration to obtain 2.0 g of methyl 2-amino-4-bromobenzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. custominsoluble were removed by filtration
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  7. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  8. additionHexane was added to the obtained residue
  9. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-4602aa96e26640be99e2088fb360a0b1
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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