Réaction #2286328

Équation de réaction

2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione

2-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione

butylamine

water

→

6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one

Rendement 74.5%

6-(4-Amino-2,6-dichlorophenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one

Rendement 74.5%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureto reflux for 1.5 h
3. 3
   FiltrationThe resulting solids were collected by filtration
4. 4
   Lavagewashed with a 1:1 solution of methanol/water (180 mL)
5. 5
   Autredried under vacuum

Mode opératoire

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.

Source