Chlorosulfonic acid → 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid
Reaction equation
[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.C([C:17]([O-:19])=[O:18])C.[Cl:20][S:21](O)(=[O:23])=[O:22]>>[Cl:20][S:21]([C:7]1[CH:6]=[CH:5][C:4]2[NH:3][C:2](=[O:1])[C:11]3[NH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[C:10]=3[C:9]=2[CH:8]=1)(=[O:23])=[O:22]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
85 mg (0.33 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate as prepared in the preceding synthesis 1 is added in the space of 90 minutes to 106 μL (1.65 mmol) of chlorosulfonic acid cooled to 0° C. on an ice bath. On completion of addition, the solution is stirred for 1 hour at room temperature then 3 hours at 70° C. The reaction mixture is cooled to room temperature then poured into ice water (20 mL). The mixture is stirred for 15 minutes then the solid is filtered, and taken up in methanol/toluene mixture. The solvents are evaporated to give 64 mg (60%) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a beige solid.
Workup
- additionOn completion of addition
- custom3 hours
- customat 70° C
- temperatureThe reaction mixture is cooled to room temperature
- stirringThe mixture is stirred for 15 minutes
- filtrationthe solid is filtered
- customThe solvents are evaporated
Sources & evidence
- ORD record
- ord-5b664e8aa71a43aeb228da7083bce479
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426437B2
Reaction notes
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