Methanol → 3-Chloro-6-methoxypyridazine

HRID 2197407Notes

Reaction equation

HRID 2197407 reaction equation
[Na].[Cl:2][C:3]1[N:4]=[N:5][C:6](Cl)=[CH:7][CH:8]=1.[CH3:10][OH:11]>>[Cl:2][C:3]1[N:4]=[N:5][C:6]([O:11][CH3:10])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 673313,6-DichloropyridazineHCID 5360545Sodium

Product 1

HCID 744033-Chloro-6-methoxypyridazine

Procedure

Sodium (4.8 g, 0.21 mol) is added portion-wise to MeOH (200 ml) with stirring. After a clear solution is formed, it is added slowly to a solution of 3,6-dichloro-pyridazine (29.6 g, 0.2 mol) in MeOH (200 ml). After addition, the mixture is heated at reflux for 3 h, then cooled and concentrated under reduced pressure. EtOAc and water are added. The organic layer is separated, dried and concentrated under reduced pressure to give 26.4 g of 3-chloro-6-methoxy-pyridazine as a white solid.

Workup

  1. customAfter a clear solution is formed
  2. additionAfter addition
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 3 h
  5. temperaturecooled
  6. concentrationconcentrated under reduced pressure
  7. additionEtOAc and water are added
  8. customThe organic layer is separated
  9. customdried
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b31924a88e5548a1a432133a8f309854
Source dataset
uspto-grants-2012_12
Patent number
US08338591B2

Reaction notes

Loading…