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

HRID 2284364Notes

Reaction equation

HRID 2284364 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 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 6-chloropyridazin-3-amine (10.2 g, 48.9 mmol) in MeOH (200 mL) was sonicated for 10 min. Sodium bicarbonate (12.97 g, 154 mmol) was added followed by slow addition of bromine (4.77 mL, 93 mmol). The reaction mixture was stirred at room temperature over night and concentrated. The residue was diluted with EtOAc and the solid was filtered. The filtrate was washed with water and brine, dried over Na2SO4, and filtered. The filtrate was concentrated to give 10.2 g crude product as a brown solid which was used for the next step without further purification. 1H NMR (400 MHz, CD3OD) δ ppm 7.93 (1H, s); LC/MS: Rt=0.75 min. LC/MS (Condition A): 208.04/210.04.

Workup

  1. customwas sonicated for 10 min
  2. concentrationconcentrated
  3. additionThe residue was diluted with EtOAc
  4. filtrationthe solid was filtered
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-030c2dc1f2d74fb49a05ad4a555487c1
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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