Acetic Acid → HCID 86627539, compound

HRID 1970040Notes

Reaction equation

HRID 1970040 reaction equation
[F: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.C(O)(=O)C.[Cl:25][S:26](O)(=[O:28])=[O:27]>>[Cl:25][S:26]([C:3]1[C:2]([F:1])=[CH:11][C:10]2[NH:9][C:8](=[O:12])[C:7]3[NH:13][CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:6]=3[C:5]=2[CH:4]=1)(=[O:28])=[O:27]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24638Chlorosulfonic acidHCID 86627540HCID 86627540, compound

Product 1

HCID 86627539HCID 86627539, compoundYield 93.5%

Conditions

Temperature
85 °C

Procedure

In a sealed tube, 601 mg (1.8 mmol) of 7-fluoro-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with one equivalent of acetic acid is dissolved in 2.4 mL (36 mmol) of chlorosulfonic acid. The reaction mixture is placed on an oil bath heated beforehand to 85° C. for 2 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 580 mg (93%) of 8-chlorosulfonyl-7-fluoro-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-9a4f7da56e0d4f589d0d3122ace8613f
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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