Sodium Carbonate → 4-Bromo-3-chlorobenzene-1,2-diamine

HRID 2101997Notes

Reaction equation

HRID 2101997 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[C:3]=1[Cl:12].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([NH2:9])[C:5]([NH2:6])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 265991564-Bromo-3-chloro-2-nitroaniline

Product 1

HCID 578001544-Bromo-3-chlorobenzene-1,2-diamineYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-bromo-3-chloro-2-nitroaniline (0.200 g, 0.797 mmol) in EtOH (100 mL), was added SnCl2-2H2O (0.9 g, 3.985 mmol). The reaction mixture was heated to reflux for 3.5 h. The cooled solution (to rt) was diluted with H2O and the pH was adjusted to ca. 10 with Na2CO3. Extraction with CHCl3 (×3), was followed by washing with brine, drying over Na2SO4, and filtration. Concentration afforded an orange solid that was dried under vacuum to obtain 0.17 g product: 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.90 (s, 2H), 3.40 (s, 2H); MS (ESI) m/z 223 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 h
  3. extractionExtraction with CHCl3 (×3)
  4. washby washing with brine
  5. dry with materialdrying over Na2SO4, and filtration
  6. concentrationConcentration
  7. customafforded an orange solid
  8. customthat was dried under vacuum

Sources & evidence

ORD record
ord-f5244fabf036461e8b8cc7bfb19a4d9c
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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