Water → 6-(4-Amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one

HRID 271199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271199
[Cl:1][C:2]1[CH:3]=[C:4]([N:21]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=1.C(N)CCC.O>CO>[NH2:21][C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([O:8][C:9]2[CH:14]=[C:13]([CH:15]([CH3:16])[CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=2)=[C:2]([Cl:1])[CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8007ButylamineHCID 598345522-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione

Produkt 1

HCID 598344456-(4-Amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-oneAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione (66) (64 g, 139.6 mmol) in methanol (500 mL) was treated with butylamine (34.67 mL, 349 mmol). The mixture was heated to reflux for 1.5 h. At this time, the reaction was cooled to room temperature and treated dropwise with water (384 mL). The resulting solids were collected by filtration, washed with a 1:1 solution of methanol/water (180 mL) followed by water (250 mL) and dried under vacuum to afford 6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one (67) (34.12 g, 74.4%) as an off-white solid; ES(+)-LRMS for C14H15Cl2N3O2 (M+H)+ at m/z=328. Exact Mass=327.0541; Molecular Weight=328.20.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with a 1:1 solution of methanol/water (180 mL)
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fc6a493a301d45e983e58a6e1cc75eda
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452882B2

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