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

HRID 1959164Notes

Reaction equation

HRID 1959164 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), ammonium chloride (150 g, 2777 mmol) dissolved in water (750 mL) and iron powder (93.3 g, 1636 mmol) were added under stirring. Resulting reaction mass was heated at 80° C. for 7 h. On completion, reaction mass was filtered through celite giving washing of water and ethyl acetate, filtrate was extracted with ethyl acetate. Combined organic layers were dried, concentrated under reduced pressure giving the desired compound.

Workup

  1. customResulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. filtrationwas filtered through celite
  5. customgiving
  6. washwashing of water and ethyl acetate, filtrate
  7. extractionwas extracted with ethyl acetate
  8. customCombined organic layers were dried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e487816237a8438aaed1bcd4441e9416
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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