Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 86027543 | HCID 86027543 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 71118729 | HCID 71118729 | 99.8% |
Reaction Steps
Sodium borohydride (2.09 g, 55.2 mmol, 1.0 eq) is added portionwise at 0° C. to a stirred suspension of (3-chloro-6-methoxy-quinolin-4-yl)-acetaldehyde (13.0 g, 55.2 mmol, 1.0 eq) in ethanol (200 mL). After 1 hour stirring at 0° C., acetone (50 mL) is added to quench the reaction. Solvents are removed and the resulting crude product is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 2-(3-chloro-6-methoxy-quinolin-4-yl)-ethanol as a yellow solid (13.1 g, 99% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321788B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-7865de9125dc41fbbadca418203300bd |
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| Source note | uspto-grants-2016_04 |
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