HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 3-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo- | HCID 10490472 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 4-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile | HCID 10563473 | 89.1% |
Reaction Steps
Mixed 122 mg (0.50 mmol) 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarbonitrile and 2.0 ml methylene chloride under N2 and kept temperature near 25° C. Added 218 μl (2.5 mmol) oxalyl chloride and 10 μl (0.125 mmol) DMF. Stirred overnight, diluted with chloroform and stirred in saturated sodium bicarbonate until basic. Separated layers and dried organics with magnesium sulfate, stripped solvent and dried in vacuo, giving 117 mg of tan solid: mass spectrum (electrospray m/e): M+H=262.8, 264.8.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06384051B1 |
| Source dataset | uspto-grants-2002_05 |
| ORD ID | ord-d1c9290b9ee34a7bb5392bdb1686107f |
| Source note | uspto-grants-2002_05 |