HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine, hydrochloride → 7-Methoxy-N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 7-Methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid | HCID 22998619 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 7-Methoxy-N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide | HCID 22998635 | 38.8% |
Reaction Steps
WSC (6.5 g) was added to an acetonitrile solution of 7-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid (3.74 g), dimethylamine hydrochloride (3.44 g), HOBt (2.85 g) and triethylamine (8.5 g). The reaction mixture was stirred at room temperature for 24 hours and concentrated. The residue was diluted with ethyl acetrate. The organic layer was washed with 1N aqueous hydrochloric acid solution, 10% aqueous potassium carbonate solution, and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were recrystallized from ethyl acetate-hexane to give the entitled compound (1.63 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329389B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-e11b771abfdd4a59ab5e738ee9b7baaa |
| Source note | uspto-grants-2001_12 |