Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 6-Quinolinecarboxylic acid, 3-bromo-, methyl ester | HCID 56636124 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58190515 | HCID 58190515 | 43.4% |
Reaction Steps
To a stirred solution of methyl 3-bromo-quinoline-6-carboxylate (1.09 g, 4 mmol) in THF (50 mL) at 0° C. was added LiAlH4 (0.155 g, 4 mmol) in small portions. The resulting mixture was stirred at 0° C. for 0.5 h. Water (0.2 mL) was added dropwise, followed by 0.2 mL of 10% aq. NaOH and 0.2 mL of water. The solid was removed and the solvent was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient to afford the title compound (413 mg, 42%). LCMS (method A): [MH]+=238/240, tR=4.453 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08507676B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-bb810b7c0c784ea1b8c4f3055e9039df |
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| Source note | uspto-grants-2013_08 |
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