Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 70496316 | HCID 70496316 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 70496444 | HCID 70496444 | 99% |
Reaction Steps
To a stirred mixture solution of 4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.7 g, 4.5 mmol) in methanol (20 mL) and tetrahydrofuran (40 mL) was added 30% sodium hydroxide in water (20 mL). The reaction mixture was stirred at 60° C. for 16 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 4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (1.4 g, 99%) as a light white solid which was used for next step without further purification: MS (ESI) M+1=351.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809369B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-2ede1a879c3047149e07f7cb4b69d037 |
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| Source note | uspto-grants-2014_08 |
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