Ammonia → HCID 86627521, compound

HRID 1970006Notes

Reaction equation

Cl[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=3[C:7]=2[CH:6]=1)(=[O:4])=[O:3].S(Cl)(Cl)=O.[NH3:26]>C(O)C>[O:15]=[C:10]1[C:9]2[NH:16][CH:17]=[CH:18][C:8]=2[C:7]2[CH:6]=[C:5]([S:2](=[O:4])(=[O:3])[NH2:26])[CH:14]=[CH:13][C:12]=2[NH:11]1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

temperatureThe solution is cooled
customthe solvents are evaporated
stirringThe reaction mixture is stirred at 70° C. for 48 hours
temperaturethen cooled to room temperature
customThe solvents are evaporated
customthe residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 85/13/2)

Sources & evidence

ORD record: ord-0012af984b26464d8c0825d6a900d760
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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