Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 4-Pyridinecarboxaldehyde | HCID 13389 | — |
| Reactant | 5-Methoxytetralone | HCID 36620 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53856658 | HCID 53856658 | 52% |
Reaction Steps
A mixture of 5-methoxy-1-tetralone (0.1 g; 0.56 mmol), pyridine-4-carboxaldehyde (91 μl ; 0.85 mmol), piperidine (16.8 μl; 0.17 mmol) and acetic acid (9.7μl ; 0.17 mmol) was heated at 130° C. for one hour. The mixture was taken up in CH2Cl2 and washed in water and in a saturated aqueous solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with CH2Cl2 /CH3CN (7/3) to give 5-methoxy-2-(4-pyridylmethylene)-1-tetralone (74 mg; 52%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05607928 |
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| Source dataset | uspto-grants-1997_03 |
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| ORD ID | ord-58075ec51ed446479de196390fbacb13 |
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| Source note | uspto-grants-1997_03 |
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