[5-Chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yl]-(2-trifluoromethyl-phenyl)-acetonitrile → 4-chloro-5-(2-trifluoromethyl-benzyl)-2H-pyridazin-3-one

HRID 2381361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381361
[Cl:1][C:2]1[C:7](=[O:8])[N:6](C2CCCCO2)[N:5]=[CH:4][C:3]=1[CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25])C#N>Cl.C(O)(=O)C.O>[Cl:1][C:2]1[C:7](=[O:8])[NH:6][N:5]=[CH:4][C:3]=1[CH2:15][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:26])([F:27])[F:25]

Komponenten

5

Edukt 1

HCID 68990773[5-Chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yl]-(2-trifluoromethyl-phenyl)-acetonitrile

Produkt 1

HCID 668754064-chloro-5-(2-trifluoromethyl-benzyl)-2H-pyridazin-3-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of [5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yl]-(2-trifluoromethyl-phenyl)-acetonitrile (550 mg, 1.38 mmol) in concentrated hydrochloric acid (8.4 mL), glacial acetic acid (2.1 mL) and water (2.1 mL) (4:1:1, 0.11 M) was heated to 120° C. overnight. After this time, the reaction was cooled to 25° C. and then poured onto ice, followed by rinsing with minimal water. The resulting aqueous mixture was brought to pH=4-5 by treatment with a 4N aqueous sodium hydroxide solution. The resulting tan solids were collected by filtration. The solids were subsequently washed with water (2×10 mL) and dried in vacuo to afford 4-chloro-5-(2-trifluoromethyl-benzyl)-2H-pyridazin-3-one (0.24 g, 62%) as a tan solid; ES+-HRMS m/e calcd for C12H8N2OF3Cl [M+H+] 289.0350, found 289.0350.

Aufarbeitung

  1. temperatureAfter this time, the reaction was cooled to 25° C.
  2. additionpoured onto ice
  3. washby rinsing with minimal water
  4. filtrationThe resulting tan solids were collected by filtration
  5. washThe solids were subsequently washed with water (2×10 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c294e6c97af44acca8a49631cd8c51d4
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258134B2

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