Hydrochloric Acid → (S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one

HRID 1527973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527973
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][C:13]=2[O:18]C)=[O:11])=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[C:13](=[O:18])[NH:14][N:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 86684800(S)-3-(4-Bromophenyl)-1-(3-methoxypyridazin-4-yl)-3-o-tolylpropan-1-one

Produkt 1

HCID 86684801(S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-oneAusbeute 108,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (S)-3-(4-bromophenyl)-1-(3-methoxypyridazin-4-yl)-3-o-tolylpropan-1-one (example 4, step 1; 312 mg, 759 μmol) in 1,4-dioxane (9 ml) was added 37% aq. hydrochloric acid solution (1.27 ml, 15.2 mmol) and the resulting solution was first stirred at 60° C. for 3 h and then for 2½ h at 80° C. After cooling the reaction mixture was poured onto ice water and ethyl acetate, neutralized with sat. aq. sodium hydrogen carbonate solution and the pH was adjusted to 6.85 with 1 M aq. potassium phosphate buffer solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound (327 mg, quantitative), which was directly used in the next step. Light red foam, MS: 397.1 [M+H]+.

Aufarbeitung

  1. waitfor 2½ h at 80° C
  2. temperatureAfter cooling the reaction mixture
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e88cb08bba59434da709ff9c82be9d36
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090565B2

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