Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Ethyl 2,5,7-trimethylquinoline-3-carboxylate | HCID 17039663 | — |
| Reactant | CID 86636910 | HCID 86636910 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58081283 | HCID 58081283 | — |
Reaction Steps
To a solution of 2,5,7-trimethylquinoline-3-carboxylic acid ethyl ester (50 mg, 0.206 mmol) in DCM (1.7 ml) at −78° C. was added DIBAI-H 1M in Toluene (29.2 mg, 0.206 mmol). Reaction mixture was stirred 1 h at −78° C. Methanol (1 ml) was added to quench the reaction at −78° C. Mixture was then warmed up to 23° C. Sat. potassium/sodium tartrate solution (Rochelle's salt, 2 ml) was added and mixture was stirred 30 min at RT. Solid was filtered off and filtrate was extracted twice with DCM. Combined organic layer was washed with sat. NaHCO3 solution, brine, dried over sodium sulfate, filtered and evaporated to afford the title compound. HPLC (Method G) Rt=1.113 min, MS (Method V) [M+H]+=202.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09290485B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-248cc8a96a504330bd71712345907167 |
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| Source note | uspto-grants-2016_03 |
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