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

HRID 2208744Notes

Reaction equation

HRID 2208744 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].[NH4+].[Cl-]>C(O)C.C(=O)(O)[O-].[Na+].[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 99.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 5-bromo-2-methyl-3-nitrobenzoate (17 g, 62.04 mmol) in ethanol (85 mL), was added NH4Cl solution (17 g in 85 mL water, 317.8 mmol) followed by Fe powder (27.82 g, 498.11 mmol). Resulting reaction mass was stirred at 90° C. for 1 h. On completion, reaction mass was filtered and filtrate was concentrated till dryness to get solid which was dissolved in saturated sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate. Combined organic layers were dried over sodium sulfate and concentrated to afford the desired compound (15 g, 99%).

Workup

  1. customResulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. filtrationwas filtered
  5. concentrationfiltrate was concentrated till dryness
  6. customto get solid which
  7. extractionAqueous layer was extracted with ethyl acetate
  8. dry with materialCombined organic layers were dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6a5aa48243e84381ab5a1207cdf40c4a
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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