Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | HCID 18629327 | HCID 18629327 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18629328 | HCID 18629328 | 76.3% |
Reaction Steps
8.3 ml of ethanol, 2.8 ml of THF and 1.5 ml of 1N hydrochloric acid were added to 275.4 mg of ethyl 1-cyclopropyl-9-methyl-8-(2-tritylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (I) and the resulting mixture was stirred at 50° C. for 2 hours. The solvent was distilled off under reduced pressure and water was added to the resulting residue and the resulting residue was washed with ethyl acetate, and thereafter, the resulting water layer was concentrated under reduced pressure. 30 ml of water, 10 ml of ethanol and 5 ml of 1N sodium hydroxide were added to the resulting residue and the resulting mixture was stirred at 50° C. for 3.5 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 120.0 mg of 1-cyclopropyl-9-methyl-8-(isoindoline-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-0b1cf6086e184310bbe363c1c5bb7405 |
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| Source note | uspto-grants-2003_02 |
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