Reaktion #1244404

ord-22102514dcb14742a2af528a0cd602d7

Reaktionsgleichung

CC(=O)[O-].[Na+]
sodium acetate
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)nnc1Cl
[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)nnc1Cl
[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)n[nH]c1=O
[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid
Ausbeute 65.0%
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)n[nH]c1=O
[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid
Ausbeute 65.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
125°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture was cooled to room temperature
  2. 2
    Einengenconcentrated
  3. 3
    workup.ADDITIONThe resulting residue was diluted with methylene chloride (200 mL)
  4. 4
    Waschenwas washed with water (150 mL)
  5. 5
    SonstigeThe organic layer was separated
  6. 6
    workup.ADDITIONHexanes (3×200 mL) were added to the residue in portions
  7. 7
    Einengensubsequently concentrated under vacuum
  8. 8
    workup.ADDITIONThe resulting semi-solid was diluted with a minimum amount of ether
  9. 9
    FiltrationThe resulting white solid was filtered
  10. 10
    Waschenwashed with cold ether
  11. 11
    Sonstigedried under high vacuum overnight

Vorschrift

A mixture of glacial acetic acid (200 mL), sodium acetate (6.1 g, 74.4 mmol) and [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid (18) (8.3 g, 21.96 mmol) was heated to 125° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with methylene chloride (200 mL) and was washed with water (150 mL). The organic layer was separated. Hexanes (3×200 mL) were added to the residue in portions and then subsequently concentrated under vacuum. The resulting semi-solid was diluted with a minimum amount of ether, scratched, and slurried. The resulting white solid was filtered, washed with cold ether and dried under high vacuum overnight to afford [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid (19) (5.1 g, 65%) as a white solid; LRMS for C15H14Cl2N2O4 (M+) m/z=357. Molecular Weight=357.1958; Exact Mass=356.0331

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07807674B2uspto-grants-2010_10