Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Thiazolidinedione | HCID 5437 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 3-Hydroxy-4-nitrobenzaldehyde | HCID 69712 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 85132866 | HCID 85132866 | 44.2% |
Reaction Steps
To a solution of 2,4-thiazolidinedione (3.50 g, 30.0 mmol) in ethanol (120 mL) was added 3-hydroxy-4-nitrobenzaldehyde (5.00 g, 30.0 mmol) and piperidine (0.44 mL, 4.50 mmol). The mixture was stirred at reflux for 15 hours and then cooled to 0° C. The resulting precipitate was collected and washed with cold ethanol to afford 3.53 g of the desired compound as a brown solid. Further concentration and precipitation of the mother liquor afforded an additional 3.1 g of the product. This was used without further purification in the next reaction. 1H NMR (CDCl3)·8.20 (1H, d, J=8.8 Hz), 7.75 (1H, s), 7.26 (1H, s), 7.12 (1H, d, J=8.8 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07414040B2 |
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| Source dataset | uspto-grants-2008_08 |
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| ORD ID | ord-02cab8cd6b154de2888300b8da58ee4b |
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| Source note | uspto-grants-2008_08 |
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