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
Reaction equation
[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[CH2:8][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(O)(=O)C>[NH2:21][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([CH2:8][C:9]2[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=2)=[C:6]([Cl:20])[CH:5]=1Participants
Conditions
- Temperature
- 25 °C
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.
Workup
- additionwas poured onto water (100 mL)
- extractionThis mixture was extracted with ethyl acetate (3×50 mL)
- washThe organics were washed with a saturated aqueous sodium chloride solution
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum to a brown oil
- customRecrystallization from diethyl ether and hexanes
Sources & evidence
- ORD record
- ord-83113a277c2440c1ae93e6daf4c9a954
- Source dataset
- uspto-grants-2016_06
- Patent number
- USRE046024E1
Reaction notes
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