Chlorosulfonic acid → HCID 86627543, compound

HRID 1970041Notes

Reaction equation

HRID 1970041 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH:15]=[CH:14][NH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.C([C:18]([O-:20])=[O:19])C.[Cl:21][S:22](O)(=[O:24])=[O:23]>>[Cl:1][C:2]1[C:3]([S:22]([Cl:21])(=[O:24])=[O:23])=[CH:4][C:5]2[C:6]3[C:15]([C:18]([OH:20])=[O:19])=[CH:14][NH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86627542HCID 86627542, compound

Product 1

HCID 86627543HCID 86627543, compoundYield 90%

Conditions

Temperature
90 °C

Procedure

In a sealed tube, 1.16 g (4 mmol) of 7-chloro-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is dissolved in 5.3 mL (80 mmol) of chlorosulfonic acid. The reaction mixture is placed on an oil bath heated beforehand to 90° C. for 6 hours, 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 1.3 g (90%) of 7-chloro-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-91e17e5f2ae94d61986f32425ca362a3
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…