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

HRID 1644192Notes

Reaction equation

HRID 1644192 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-1e4e56e1832a4ccca885b1d4055d6c0c
Source dataset
uspto-grants-2012_02
Patent number
US08124604B2

Reaction notes

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