HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Chlorobenzylamine → 5-Fluoro-N-[[4-chlorophenyl]methyl]-8-hydroxy-7-quinolinecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Chlorobenzylamine | HCID 66036 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 5-Fluoro-8-hydroxyquinoline-7-carboxylic acid | HCID 18372564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Fluoro-N-[[4-chlorophenyl]methyl]-8-hydroxy-7-quinolinecarboxamide | HCID 18372513 | 41.7% |
Reaction Steps
To a solution of 5-fluoro-8-hydroxyquinoline-7-carboxylic acid (0.311 g) of Preparation 4 and 4-chlorobenzylamine (0.219 g) in 20 mL DMF is added 1-(3-di-methylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.305 g) and 1-hydroxy-benzotriazole monohydrate (0.217 g). The mixture is stirred overnight. The solution is then poured into 30 mL ice-water. The resulting solid is collected and dried. The crude product is recrystallized from EtOAc/hexanes to yield 0.207 g of the title product as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06500842B1 |
| Source dataset | uspto-grants-2002_12 |
| ORD ID | ord-ef415df9fb254dc5abbf13ef15ad637e |
| Source note | uspto-grants-2002_12 |