Reaction #2286349

Reaction equation

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

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

→

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

Yield 69.0%

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

Yield 69.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   workup.ADDITIONwas poured onto water (100 mL)
2. 2
   ExtractionThis mixture was extracted with ethyl acetate (3×50 mL)
3. 3
   WashThe organics were washed with a saturated aqueous sodium chloride solution
4. 4
   Dryingdried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under vacuum to a brown oil
7. 7
   OtherRecrystallization from diethyl ether and hexanes

Procedure

A solution of 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-isoindole-1,3-dione (93) (300 mg, 0.66 mmol) in glacial acetic acid was heated to 110° C. for 3 h. At this time, the reaction was cooled to 25° C. and was poured onto water (100 mL). This mixture was extracted with ethyl acetate (3×50 mL). The organics were washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum to a brown oil. Recrystallization from diethyl ether and hexanes followed by flash chromatography (Merck Silica gel 60, 230-400 mesh, 30:70 ethyl acetate/petroleum ether) afforded 6-(4-amino-2,6-dichloro-benzyl)-4-isopropyl-2-methyl-2H-pyridazin-3-one (94) (148 mg, 69%) as an off-white solid; ES_HRMS m/e calcd for C15H17Cl2N3O (M+H)+ 326.0822, found 326.0822. Exact Mass=325.0749; Molecular Weight=326.2282.

Source