Hydrochloric Acid → 5-(2-acetyl-phenoxy)-4-chloro-2H-pyridazin-3-one

HRID 2381326Notes

Reaction equation

HRID 2381326 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][C:7]1[CH:12]=[N:11][N:10](C2CCCCO2)[C:9](=[O:19])[C:8]=1[Cl:20])(=[O:3])[CH3:2].Cl.O>CO>[C:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][C:7]1[CH:12]=[N:11][NH:10][C:9](=[O:19])[C:8]=1[Cl:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 668754605-(2-acetyl-phenoxy)-4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one

Product 1

HCID 668750665-(2-acetyl-phenoxy)-4-chloro-2H-pyridazin-3-oneYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-(2-acetyl-phenoxy)-4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (15.0 g, 0.043 mol), concentrated hydrochloric acid (30 mL), water (45 mL) and methanol (130 mL) was heated at reflux for 2 h. At this time, the reaction was concentrated in vacuo. The residue was charged with water (200 mL) and then basified with a saturated aqueous sodium bicarbonate solution. The resulting material was collected by filtration, rinsed with water and petroleum ether, and dried to afford 5-(2-acetyl-phenoxy)-4-chloro-2H-pyridazin-3-one (9.0 g, 79%); ESI-MS 265 [M+H+].

Workup

  1. temperatureat reflux for 2 h
  2. concentrationAt this time, the reaction was concentrated in vacuo
  3. additionThe residue was charged with water (200 mL)
  4. filtrationThe resulting material was collected by filtration
  5. washrinsed with water and petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-e0c09a82977b4ae9907d8c9e4a979f56
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…