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

HRID 68445

Reaction equation

HRID 68445 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-4e3baff1832d4fa7abb52f3c6518eb96
Source dataset
uspto-grants-2014_09
Patent number
US08822457B2

Linked notes

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