2-(Methylamino)ethanol → 2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol

HRID 454116Notes

Reaction equation

HRID 454116 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[Cl:9].[CH3:10][NH:11][CH2:12][CH2:13][OH:14]>C(O)(C)C>[Cl:9][C:3]1[N:4]=[N:5][C:6]([Cl:8])=[CH:7][C:2]=1[N:11]([CH2:12][CH2:13][OH:14])[CH3:10]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 220306484-Bromo-3,6-dichloropyridazine

Product 1

HCID 220307752-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanolYield 90.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-bromo-3,6-dichloro-pyridazine (1.11 g, 5 mmol), (J. Chem. Soc., Perkin Trans I, 1974, 696), and 2-(methylamino)ethanol (0.75 g, 10 mmol) in isopropanol (10 ml) was heated at reflux for 30 minutes. The solvent was removed by evaporation, the residue was partitioned between methylene chloride and water and the aqueous layer was adjusted to pH9 with solid potassium carbonate. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, collected by filtration and dried under vacuum to give 2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol (1 g, 90%).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent was removed by evaporation
  3. customthe residue was partitioned between methylene chloride and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was triturated with ether
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-eaca31b71fe5436fb1cbd55ab81aa0d5
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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