Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | HCID 18629326 | HCID 18629326 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18629339 | HCID 18629339 | 67.6% |
Reaction Steps
6.0 ml ethanol, 2.0 ml of THF and 1.0 ml of 1N hydrochloric acid were added to 248.0 mg of ethyl 1-cyclopropyl-9-methoxy-8-(1-methyl-2-tritylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (XIV) and the resulting mixture was stirred at a room temperature for 30 minutes. The solvent was distilled off under reduced pressure and water was added to the resulting residue, which was washed with ethyl acetate, and thereafter, the resulting water layer was concentrated under reduced pressure. 10 ml of water, 5 ml of ethanol and 3 ml of 1N sodium hydroxide were added to the residue and the resulting mixture was stirred at 50° C. for 3 hours. The reaction solution was concentrated under reduced pressure, and thereafter, dissolved in 4 ml of water and neutralized with 1N hydrochloric acid. The precipitated crystal was separated by filtering to obtain 99.1 mg of 1-cyclopropyl-9-methoxy-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06525066B2 |
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| Source dataset | uspto-grants-2003_02 |
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| ORD ID | ord-05238b429778445f9e0e89b3952a64fc |
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| Source note | uspto-grants-2003_02 |
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