Hydrochloric Acid → 4,5-Dibromo-2-(4-fluorophenyl)pyridazin-3(2H)-one

HRID 891320

Reaktionsgleichung

Reaktionsgleichung von HRID 891320
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Br:5])/[Br:3].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1.Cl>C(O)(=O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:6](=[O:7])[C:4]([Br:5])=[C:2]([Br:3])[CH:1]=[N:18]2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 69982(4-Fluorophenyl)hydrazineHCID 3033972Mucobromic Acid

Produkt 1

HCID 14768284,5-Dibromo-2-(4-fluorophenyl)pyridazin-3(2H)-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

Mucobromic acid (5.0 g, 19.4 mmol) dissolved in acetic acid (110 mL) was treated with 4-fluorophenyl hydrazine.HCl, and the heterogeneous mixture brought to reflux at a bath temperature of 115° C. for 15 hours. During the course of reaction, the mixture became a homogeneous deep red solution, and upon cooling to 23° C., a crystalline precipitate formed. The solution was poured into ice water (1000 mL) and stirred for 20 minutes. The yellow/brown crystals were filtered off, washed with additional cold water, and dried in vacuo to provide 5.8 g (86%) of product. (J. Het. Chem., 1993, 30, 1501; Heterocycles 1985, 23, 2603) 1H NMR (300 MHz, DMSO-d6) δ 7.31-7.41 (m, 2H), 7.57-7.64 (m, 2H), 8.29 (s, 1H). MS (DCI+) m/z 347 (Br79Br79 M+H)+, m/z 349 (Br79Br81 M+H)+, m/z 364 (Br79Br79 M+NH4)+, and m/z 366 (Br79Br81 M+NH4)+.

Aufarbeitung

  1. customDuring the course of reaction
  2. temperatureupon cooling to 23° C.
  3. customa crystalline precipitate formed
  4. filtrationThe yellow/brown crystals were filtered off
  5. washwashed with additional cold water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-21c8a73fde0f4d4caa4b1ced22c0cd4b
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001895B2

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