Chloroacetone → 2,6-Dimethylimidazo[1,2-b]pyridazine

HRID 226023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226023
[NH2:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Cl[CH2:10][C:11](=O)[CH3:12].C([O-])(O)=O.[Na+]>CCO>[CH3:12][C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][N:3]2[CH:10]=1

Komponenten

5

Edukt 3

HCID 6571ChloroacetoneHCID 877126-Methylpyridazin-3-amineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 218176672,6-Dimethylimidazo[1,2-b]pyridazineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-amino-6-methyl-pyridazine (4.53 g, 41.58 mmol) in EtOH (60 mL) is treated with chloroacetone (3.5 mL, 43.66 mmol). The reaction is refluxed overnight. While it is hot, NaHCO3 (8.7 g, 103.9 mmol) is added in portions. The resulting mixture is refluxed for 2 h. It is cooled to rt and filtered through silical gel, washed with EtOAc, and concentrated. Purification of the crude material by chromatography gives the title compound (3.1 g, 21.11 mmol, 51%). 1H NMR (CDCl3): δ 2.49 (s, 3H), 2.55 (s, 3H), 6.84 (d, J=9.3 Hz, 1H), 7.64 (s, 1H), 7.70 (d, J=9.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C8H9N3 (M+H)+: 148.2. found: 148.1.

Aufarbeitung

  1. temperatureThe reaction is refluxed overnight
  2. temperatureThe resulting mixture is refluxed for 2 h
  3. filtrationfiltered through silical gel
  4. washwashed with EtOAc
  5. concentrationconcentrated
  6. customPurification of the crude material by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d8c34bddadeb48b6a48b90880cda2565
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

Notizen zur Reaktion

Wird geladen…