Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 86696579 | HCID 86696579 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 56959243 | HCID 56959243 | — |
Reaction Steps
A solution of ethyl 1-cyclopropyl-8-(4-chloro-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (95 mg, 0.249 mmol) in THF (6 mL) and water (2 mL) was treated with LiOH (43 mg, 1.02 mmol). The reaction was heated to 60° C. for 4 h and acidified with 1N HCl to pH 4. The precipitate was dissolved with ethyl acetate (50 mL) and washed with brine (2×20 mL). The organic phase was separated, dried, and concentrated. The precipitate was filtered to afford the title compound EXAMPLE 45 as yellow solid (49 mg, 56%). ESI-MS m/z: 354 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.34 (d, J=7.2 Hz, 1H), 8.27 (s, 1H), 7.68-7.56 (m, 5H), 2.84 (s, 3H), 2.55-2.52 (m, 1H), 2.39 (s, 3H), 1.08-1.05 (m, 2H), 0.80-0.78 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962842B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-55439319b8c74391a72da16efdf1793f |
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| Source note | uspto-grants-2015_02 |
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