Ammonium Chloride → Methyl 3-Amino-5-bromo-2-methylbenzoate

HRID 1959199Notes

Reaction equation

HRID 1959199 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:13][C:4]1[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([Br:1])[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 24727998Methyl 5-bromo-2-methyl-3-nitrobenzoate

Product 1

HCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-2-methyl-3-nitrobenzoate (150 g, 544 mmol) in ethanol (750 mL) was added ammonium chloride (150 g, 2777 mmol) dissolved in water (750 mL) and iron powder (93.3 g, 1636 mmol) with stirring. The resulting reaction mixture was heated at 80° C. for 7 h. On completion, the reaction mixture was filtered through celite; the residue was washed with water and ethyl acetate, filtrate was extracted with ethyl acetate. The combined organic layers were dried, concentrated under reduced pressure to give methyl 3-amino-5-bromo-2-methylbenzoate which was used directly in the next step.

Workup

  1. customThe resulting reaction mixture
  2. filtrationOn completion, the reaction mixture was filtered through celite
  3. washthe residue was washed with water and ethyl acetate, filtrate
  4. extractionwas extracted with ethyl acetate
  5. customThe combined organic layers were dried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f696c67f89b948f3a4c33580642b2297
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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