6-Amino-3-chloropyridazine → 3-Amino-4-bromo-6-chloropyridazine

HRID 2069779Notes

Reaction equation

HRID 2069779 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[Br:14]Br>CO>[Br:14][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[NH2:8]

Participants

5

Reactant 3

HCID 216436-Amino-3-chloropyridazineHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 220244193-Amino-4-bromo-6-chloropyridazineYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-Chloro-pyridazin-3-ylamine (4 g, 31 mmol) in methanol (60 mL) was added NaHCO3 (5.2 g, 62 mmol). The reaction mixture was stirred for 30 minutes at RT then Br2 (4.9 g, 31 mmol) was added drop wise. Then the resulting reaction mixture was stirred additionally for 16 h at RT. After completion of reaction, the reaction mass concentrated under reduced pressure, crude purified by silica gel (100-200 mesh) chromatography using EtOAc/Hexane (8:2) to afford 4-Bromo-6-chloro-pyridazin-3-ylamine (2.3 g, 36%) as a solid.

Workup

  1. customThen the resulting reaction mixture
  2. stirringwas stirred additionally for 16 h at RT
  3. customAfter completion of reaction
  4. concentrationthe reaction mass concentrated under reduced pressure, crude
  5. custompurified by silica gel (100-200 mesh) chromatography

Sources & evidence

ORD record
ord-45e9fddab1de40c3b84629aeff71ab43
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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