Sulfuric Acid → 1-Chloroisoquinoline-5-sulfonic acid

HRID 2118498Notes

Reaction equation

HRID 2118498 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[S:12](=O)(=[O:15])([OH:14])[OH:13]>>[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([OH:15])(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 137300201-Chloroisoquinoline-5-sulfonic acid

Procedure

145 g of 1-Chloroisoquinoline was dropwise added to 500 g of 60% fuming sulfuric acid while cooling with ice. Then, the temperature was elevated to 80° C. and the reaction was effected while stirring for 18 hours. The obtained reaction mixture was added to 1 kg of ice water, followed by stirring for 2 hours at 5° C. to precipitate crystals. The thus obtained crystals were separated by filtration, washed with 100 ml of methanol and then with 100 ml of ether, and dried under reduced pressure to obtain 126 g of 1-chloro-5-isoquinolinesulfonic acid. The compound was analyzed to give the following data.

Workup

  1. temperaturewhile cooling with ice
  2. customwas elevated to 80° C.
  3. customThe obtained reaction mixture
  4. stirringby stirring for 2 hours at 5° C.
  5. customto precipitate crystals
  6. customThe thus obtained crystals were separated by filtration
  7. washwashed with 100 ml of methanol
  8. dry with materialwith 100 ml of ether, and dried under reduced pressure

Sources & evidence

ORD record
ord-1e9e04c01d3044849af7ef983ebe8a81
Source dataset
uspto-grants-1987_07
Patent number
US04678783

Reaction notes

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