Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 67442803 | HCID 67442803 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67441218 | HCID 67441218 | 44% |
Reaction Steps
A mixture of 2-(3,5-difluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.0 g, 6.1 mmol), lithium hydroxide hydrate (2.57 g, 61 mmol), water (5 mL) in methanol (10 mL) and tetrahydrofuran (20 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3,5-difluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.84 g, 44%) as a white solid which was used for next step without further purification: LC/MS m/e calcd for C18H17F2NO2 (M+H)+: 318.3, observed: 318.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586747B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-65e8e1f072f544328a2be9b3a5f389fa |
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| Source note | uspto-grants-2013_11 |
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