Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid | HCID 45121068 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86627521 | HCID 86627521 | 3% |
Reaction Steps
In a sealed tube, 490 mg (1.5 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 2) is dissolved in 1.5 mL of an aqueous solution of ammonia at 28%. The mixture is stirred at 100° C. for 4 hours. The solution is cooled then the solvents are evaporated. The residue is taken up in 10 mL of anhydrous ethanol. A solution of 1.1 mL (15 mmol) of thionyl chloride in 4.5 mL of anhydrous ethanol is then added slowly. The reaction mixture is stirred at 70° C. for 48 hours then cooled to room temperature. The solvents are evaporated and the residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 85/13/2) to give 18 mg (3%) of 4-oxo-8-sulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08426437B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-0012af984b26464d8c0825d6a900d760 |
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| Source note | uspto-grants-2013_04 |
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