Hydrochloric Acid → 6-(1-benzofuran-5-yl)-4-carboxy-2H-pyridazin-3-one
Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=O)[CH3:2].O=[C:14]([C:20]([O:22]CC)=[O:21])[C:15](OCC)=[O:16].O.[NH2:26][NH2:27].[OH-].[Na+].Cl>C(O)(C)C>[O:11]1[C:7]2[CH:6]=[CH:5][C:4]([C:1]3[CH:2]=[C:14]([C:20]([OH:22])=[O:21])[C:15](=[O:16])[NH:26][N:27]=3)=[CH:12][C:8]=2[CH:9]=[CH:10]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
5-Acetyl-1-benzofuran (536 mg, 3.35 mmol) and diethyl ketomalonate (642 mg, 3.69 mmol) were mixed together, and the mixture was stirred for 34 hours at 120° C. Hydrazine monohydrate (247 mg, 4.93 mmol) was added to a solution of the reaction mixture in isopropanol (8.5 mL), and the resultant mixture was heated with stirring for six hours at 100° C. A 2-mol/L aqueous sodium hydroxide solution (5.2 mL) was added thereto, and the mixture was further stirred for four hours at 100° C. The mixture was cooled with ice, and concentrated hydrochloric acid was added thereto, to thereby acidify the heated system. The formed precipitates were collected through filtration, thoroughly washed with water, and dried, to thereby yield 397 mg of the title compound as a yellow powder (46.2%).
Workup
- stirringwith stirring for six hours at 100° C
- stirringthe mixture was further stirred for four hours at 100° C
- additionwas added
- customThe formed precipitates
- filtrationwere collected through filtration
- washthoroughly washed with water
- customdried
Sources & evidence
- ORD record
- ord-017e90636fa94908a46b0d4de27df207
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07314877B2
Reaction notes
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