Pyridine → 4-oxo-8-phenylsulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

HRID 1969934Notes

Reaction equation

HRID 1969934 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[S:15]([C:18]1[CH:27]=[CH:26][C:25]2[NH:24][C:23](=[O:28])[C:22]3[NH:29][CH:30]=[C:31]([C:32]([OH:34])=[O:33])[C:21]=3[C:20]=2[CH:19]=1)(=[O:17])=[O:16]>ClCCl.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>[O:28]=[C:23]1[C:22]2[NH:29][CH:30]=[C:31]([C:32]([OH:34])=[O:33])[C:21]=2[C:20]2[CH:19]=[C:18]([S:15](=[O:17])(=[O:16])[NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:27]=[CH:26][C:25]=2[NH:24]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 451210694-oxo-8-phenylsulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acidYield 43.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

30 μL (0.37 mmol) of pyridine and 20 μL (0.22 mmol) of aniline are added to 60 mg (0.18 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid suspended in 4 mL of anhydrous dichloromethane and 1 mL of anhydrous dimethylformamide. The reaction mixture is stirred for 5 hours at room temperature then diluted with a 10% aqueous solution of potassium carbonate and dichloromethane. The phases are separated and the aqueous phase is acidified with acetic acid to pH of 4. The product is extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered then evaporated. The residue is diluted with water (5 mL) then the solid is filtered and dried under vacuum to give 30 mg (42%) of 4-oxo-8-phenylsulfamoyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a beige solid.

Workup

  1. customThe phases are separated
  2. extractionThe product is extracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customthen evaporated
  6. additionThe residue is diluted with water (5 mL)
  7. filtrationthe solid is filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e71c9f14b0dc4af7b9e6064df8a4ed2a
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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