(Phenylmethyl)hydrazine → 3,4-Dichloro-6-phenylpyridazine

HRID 911187

Reaktionsgleichung

Reaktionsgleichung von HRID 911187
[O:1]=[C:2](CCC1C=CC=CC=1)C(O)=O.C1(CNN)C=CC=CC=1.[Cl:23][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[Cl:30].[CH3:37][O-:38].[Na+]>CO>[Cl:23][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[Cl:30].[CH3:2][O:1][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[O:38][CH3:37].[CH3:2][O:1][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[Cl:30]

Komponenten

8

Edukt 4

HCID 11157(Phenylmethyl)hydrazineHCID 697322-Oxo-4-phenylbutyric acidHCID 10942334Sodium MethoxideHCID 131632313,4-Dichloro-6-phenylpyridazine

Produkt 3

HCID 131632313,4-Dichloro-6-phenylpyridazineHCID 13342056HCID 13342056, VerbindungHCID 667319983-Methoxy-4-chloro-6-phenylpyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

3,4-Dichloro-6-phenylpyridazine was synthesized from □-oxobenzenebutanoic acid and 1-(phenylmethyl)hydrazine in 2 steps according to a procedure by Sircar (Sircar, l. J. Het. Chem. 1983, 20, 1473-1476.) 3,4-Dichloro-6-phenylpyridazine (100 mg, 0.44 mmol) was combined with sodium methoxide (1.1 mL of a 0.50M solution in methanol, 0.55 mmol, 1.25 equiv.) and methanol (296 μl, 1.5M) in a resealable tube and heated to 65° C. for 1 hour. The methanol was evaporated in vacuo, and water was added to the residue. The mixture was extracted with DCM, dried over K2CO3, filtered and concentrated in vacuo, to afford 3,4-dimethoxy-6-phenylpyridazine and 3-methoxy-4-chloro-6-phenylpyridazine, the title compound, as a solid.

Aufarbeitung

  1. customThe methanol was evaporated in vacuo, and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with DCM
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4ca99aa7296b42039236b89cae8f23a9
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022221B2

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