Hydrochloric Acid → 6-(3-Hydroxy-benzofuran-2-sulfonyl)-2H-pyridazin-3-one
Reaction equation
C[O:2][C:3]1[N:4]=[N:5][C:6]([S:9]([C:12]2[O:13][C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[C:16]=2[OH:17])(=[O:11])=[O:10])=[CH:7][CH:8]=1.Cl>O1CCOCC1>[OH:17][C:16]1[C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[O:13][C:12]=1[S:9]([C:6]1[CH:7]=[CH:8][C:3](=[O:2])[NH:4][N:5]=1)(=[O:11])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3-methoxy-6-(3-hydroxy-benzofuran-2-sulfonyl)-pyridazine (2.7 mmol, 820 mg), conc. HCl (2 mL), and dioxane (10 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled and evaporated to dryness. The dried residue was extracted with EtOAc (2×20 mL). The extract was dried, filtered, and the filtrate was evaporated to a residue, which was purified by silica gel chromatography (eluent:EtOAc:n-hexanes::3:1), triturated with water (10 mL), and filtered to obtain the desired product: 6-(3-hydroxy-benzofuran-2-sulfonyl)-2H-pyridazin-3-one (35%, 284 mg); mp 186° C.-189° C.
Workup
- temperatureThe reaction mixture was cooled
- customevaporated to dryness
- extractionThe dried residue was extracted with EtOAc (2×20 mL)
- customThe extract was dried
- filtrationfiltered
- customthe filtrate was evaporated to a residue, which
- customwas purified by silica gel chromatography (eluent:EtOAc:n-hexanes::3:1)
- customtriturated with water (10 mL)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-bd0ac02aa2a14ceeb9549e3b164b7d05
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06849629B2
Reaction notes
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