Bromine → 4-Bromo-6-phenylpyridazin-3-amine

HRID 1755307Notes

Reaction equation

HRID 1755307 reaction equation
[C:1]1([C:7]2[N:12]=[N:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[Br:19]Br>CO>[Br:19][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:12]=[N:11][C:10]=1[NH2:13]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 119589156-Phenylpyridazin-3-amine

Product 1

HCID 583863604-Bromo-6-phenylpyridazin-3-amineYield 33.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 150 mL round bottom flask was placed 6-phenylpyridazin-3-amine (2.5 g, 14.5 mmol), NaHCO3 (2.44 g, 29 mmol) and methanol (50 mL) then to this suspension was added Br2 (2.317 g, 14.5 mmol) drop wise over about 30 minutes at room temperature. The mixture was stirred for 16 h, then filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=2:1) to give 4-bromo-6-phenylpyridazin-3-amine (1.2 g, 33%) as a light orange solid. LC-MS: [M+H]+, 250.0, tR=1.487 min.

Workup

  1. customIn a 150 mL round bottom flask was placed
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-dc69f5c8911d47afb49c0a67735122db
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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