HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thiazolidinedione → 5-[8-Methoxy-1-(4-methoxycarbonyl benzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thiazolidinedione | HCID 5437 | — |
| Reactant | 1-(4-Carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde | HCID 86613925 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Catalyst | Piperidine | HCID 8082 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 5-[8-Methoxy-1-(4-methoxycarbonyl benzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione | HCID 86613941 | 90% |
Reaction Steps
7.0 g of 8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde and 3.25 g of 2,4-thiazolidinedione were suspended in 70 ml of toluene. Ten drops of piperidine and ten drops of acetic acid were added, followed by heating and refluxing for 4 hours. The resultant was allowed to cool to precipitate a solid, and the precipitated solid was collected by filtration and dried, giving 8.0 g (90% yield) of 5-[8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethylidene]thiazolidine-2,4-dione as a light yellow powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08362252B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-126f021bd8a941ee8568e13c31910473 |
| Source note | uspto-grants-2013_01 |