Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 70896141 | HCID 70896141 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 70896138 | HCID 70896138 | 73.1% |
Reaction Steps
To a solution of ethyl 7-bromo-6-methoxyquinoline-3-carboxylate (250 mg, 0.80 mmol) in tetrahydrofuran (5 mL) was added 1 N aqueous lithium hydroxide (1.6 mL, 1.6 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and the residue was taken up in water and 1 N aqueous lithium hydroxide (0.4 mL). The solution was extracted twice with ethyl acetate. The aqueous layer was then acidified to pH=4 with 1 N aqueous hydrochloric acid. The resulting precipitate was filtered, washed with water, and dried under vacuum to give the title compound (165 mg, 73%) as an off-white solid. +ESI (M+H+1) 284.1; 1H NMR (400 MHz, CD3OD, δ): 9.19 (d, J=2.15 Hz, 1 H), 8.89 (d, J=1.76 Hz, 1 H), 8.30 (s, 1 H), 7.53 (s, 1 H), 4.04 (s, 3 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802688B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-97154060bb204fd0896069f3aa618260 |
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| Source note | uspto-grants-2014_08 |
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