Acetic Acid → 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

HRID 1970014Notes

Reaction equation

HRID 1970014 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.C(O)(=O)C.[Cl:24][S:25](O)(=[O:27])=[O:26]>>[Cl:24][S:25]([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:27])=[O:26]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24638Chlorosulfonic acidHCID 86627461HCID 86627461, compound

Product 1

HCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acidYield 100%

Conditions

Temperature
85 °C

Procedure

In a sealed tube, 1.42 g (4.5 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with one equivalent of acetic acid (synthesis 1) is dissolved in 6 mL (90 mmol) of chlorosulfonic acid. The reaction mixture is placed on an oil bath heated beforehand to 85° C. for 20 minutes, cooled on an ice bath then poured slowly onto crushed ice. The solid is filtered, rinsed with water, diisopropyl ether and pentane then dried under vacuum to give 1.47 g (quantitative) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a brown solid.

Workup

  1. customThe reaction mixture is placed on an oil bath
  2. temperaturecooled on an ice bath
  3. additionthen poured slowly
  4. customonto crushed ice
  5. filtrationThe solid is filtered
  6. washrinsed with water, diisopropyl ether and pentane
  7. customthen dried under vacuum

Sources & evidence

ORD record
ord-1f2d7e73156c4b29ae8552878a989113
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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