반응 #2286349

반응 방정식

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

수율 69.0%

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

수율 69.0%

용매

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONwas poured onto water (100 mL)
2. 2
   추출This mixture was extracted with ethyl acetate (3×50 mL)
3. 3
   세척The organics were washed with a saturated aqueous sodium chloride solution
4. 4
   건조dried with magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated under vacuum to a brown oil
7. 7
   기타Recrystallization from diethyl ether and hexanes

실험 절차

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.

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