Formic Acid → 5-(2-acetyl-phenoxy)-2H-pyridazin-3-one

HRID 2381327Notes

Reaction equation

HRID 2381327 reaction equation
[C:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:12]=[N:11][NH:10][C:9](=[O:13])[C:8]=1Cl)(=[O:3])[CH3:2].C(O)=O.C([O-])=O.[NH4+]>[Pd].C(O)C>[C:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:12]=[N:11][NH:10][C:9](=[O:13])[CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723923Ammonium formate2×HCID 668750665-(2-acetyl-phenoxy)-4-chloro-2H-pyridazin-3-one

Product 1

HCID 668758165-(2-acetyl-phenoxy)-2H-pyridazin-3-oneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 5-(2-acetyl-phenoxy)-4-chloro-2H-pyridazin-3-one (6 g, 0.0227 mol) and palladium on carbon (2.5 g) in ethanol (180 mL) was heated to reflux and then treated with formic acid (1.2 g, 0.023 mol). The reaction stirred for 10 min at reflux and then ammonium formate (1.43 g, 0.023 mol) was added. The reaction stirred at reflux for another 10 min. At this time, a second portion of ammonium formate (0.3 g, 0.0048 mol) was added. After 5 min, the reaction was cooled to 25° C. and filtered. The filtrate was concentrated in vacuo to afford 5-(2-acetyl-phenoxy)-2H-pyridazin-3-one (4.7 g, 90%); ESI-MS 231 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. stirringThe reaction stirred
  5. temperatureat reflux for another 10 min
  6. waitAfter 5 min
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9a25442540ed4b5e81e3feea428bd71b
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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