HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,6-Dihydroxyquinoline | HCID 177065 | — |
| Reactant | 1-chloro-2-hydroxy-3-(N-methyl-N-benzylamino)propane | HCID 14719871 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril | HCID 10359775 | 22.6% |
Reaction Steps
To a solution of 6-hydroxycarbostyril (1.6 g) and sodium hydride (50% oily) (1 g) in dimethylformamide (30 ml), 1-chloro-2-hydroxy-3-(N-methyl-N-benzylamino)propane (2.2 g) is added dropwise at room temperature. After the addition, the mixture is heated with stirring at 70°-80° C. for 3 hours. The reaction mixture is poured into water and extracted with chloroform, and the extract is dried over magnesium sulfate. Chloroform is distilled off and the resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25) and recrystallized from ethanol to give 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril (0.76 g), as white powder, m.p. 129°-132° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05266577 |
| Source dataset | uspto-grants-1993_11 |
| ORD ID | ord-70dc53cb0caa4c349a38943c1a0601aa |
| Source note | uspto-grants-1993_11 |