Hydrochloric Acid → 4-Carboxy-6-(2,3-dihydro-1-benzofuran-5-yl)-2H-pyridazin-3-one
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7]2)(=O)[CH3:2].O=[C:14]([C:20]([O:22]CC)=O)[C:15]([O:17]CC)=[O:16].O.[NH2:26][NH2:27].[OH-].[Na+].Cl>C(O)(C)C>[C:15]([C:14]1[C:20](=[O:22])[NH:26][N:27]=[C:1]([C:4]2[CH:12]=[CH:11][C:10]3[O:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[CH:2]=1)([OH:17])=[O:16]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
5-Acetylcoumarane [Brown H. C., Inukai T., J. Am. Chem. Soc., 83 4825 (1961)] (5.0 g, 30.8 mmol) and diethyl ketomalonate (5.9 g, 33.9 mmol) were mixed together, and the mixture was stirred for 39 hours at 120° C. The reaction mixture was dissolved in isopropanol (100 mL), and hydrazine monohydrate (3.38 g, 67.5 mmol) was added to the resultant mixture, followed by stirring for six hours at 100° C. A 2-mol/L aqueous sodium hydroxide solution (7 mL) was added thereto, and the resultant mixture was stirred for four hours at 100° C. The reaction mixture was cooled on ice and acidified with concentrated hydrochloric acid. The formed precipitates were collected through filtration and thoroughly washed with water, followed by drying, to thereby yield 5.9 g of the title compound as a yellow powder (74.1%).
Workup
- stirringby stirring for six hours at 100° C
- temperatureThe reaction mixture was cooled on ice
- customThe formed precipitates
- filtrationwere collected through filtration
- washthoroughly washed with water
- customby drying
Sources & evidence
- ORD record
- ord-32d8b6f1efa241a8a309b2c112601c50
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07314877B2
Reaction notes
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