Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester | HCID 67442796 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 67441465 | HCID 67441465 | 88.1% |
Reaction Steps
A mixture of 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (8.7 g, 26.8 mmol) in methanol (80 mL) and tetrahydrofuran (100 mL), 30% sodium hydroxide in water (50 mL) 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 (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (7 g, 88%) as a brown solid which was used for next step without further purification: LC/MS m/e calcd for C18H20N2O2 (M+H)+: 297.37, observed: 297.2.
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-67211f3a92834fa7ba3b2e5fb85cdc99 |
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| Source note | uspto-grants-2013_11 |
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