HuagongsheHuagongshe Chemistry Print Report · For research reference only
8-Hydroxyquinoline-7-carboxylic Acid → N-[5-(3-chlorophenyl)-4-oxo-1,3-thiazol-2-yl]-8-hydroxyquinoline-7-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 8-Hydroxyquinoline-7-carboxylic Acid | HCID 231363 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 2-Amino-5-(3-chlorophenyl)-4-hydroxy-1,3-thiazole | HCID 18372630 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-[5-(3-chlorophenyl)-4-oxo-1,3-thiazol-2-yl]-8-hydroxyquinoline-7-carboxamide | HCID 178522601 | 30.5% |
Reaction Steps
To a solution of 8-hydroxyquinoline-7-carboxylic acid (0.284 g) of Preparation 1 and 2-amino-5-(3-chlorophenyl)-4-hydroxy-1,3-thiazole (0.340 g) in 20 mL DMF is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.305 g) and 1-hydroxybenzotriazole monohydrate (0.217 g). The mixture is stirred at room temperature for 7 days. The solution is then poured into 30 mL ice-water. The resulting solid is collected and dried. The crude product is triturated with hot EtOAc, then with hot i-PrOH to yield 0.182 g of the title product as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06211376B1 |
| Source dataset | uspto-grants-2001_04 |
| ORD ID | ord-9d1f2101e04c4c22ae46ec6adc5e0c49 |
| Source note | uspto-grants-2001_04 |