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

HRID 2208915Notes

Reaction equation

HRID 2208915 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-methylbenzoateYield 132.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of above crude compound methyl 5-bromo-2-methyl-3-nitrobenzoate (150 g, 0.54 mol) in ethanol (750 mL), ammonium chloride (150 g, 2.78 mol) dissolved in 750 ml of water was added followed by iron powder (93.3 g, 1.64 mol) with vigorous stirring. The mixture was heated at 80° C. for 7 hand filtered through celite. The filter pad was washed with water and ethyl acetate and the filtrates were extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the title compound (175 g crude).

Workup

  1. additionwas added
  2. filtrationfiltered through celite
  3. washThe filter pad was washed with water and ethyl acetate
  4. extractionthe filtrates were extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a71824a8d5b4448a72a57cf5279ae2f
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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