Sulfuric Acid → 1-Chloroisoquinoline-5-sulfonic acid

HRID 1067238Notes

Reaction equation

HRID 1067238 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][N:8]=1>>[Cl:6][C:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([S:1]([OH:3])(=[O:5])=[O:2])[C:11]=2[CH:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 137300201-Chloroisoquinoline-5-sulfonic acid

Conditions

Temperature
80 °C

Procedure

To an ice-cold solution of fuming sulphuric acid (20% SO3, 2 mL) was added 1-chloroisoquinoline (1.0 g, 6.1 mmol) portionwise with stirring. After stirring at room temperature for 3 hours, the reaction was heated at 80° C. for 18 h, then cooled in an ice bath, poured onto ice (70 g), washed with ether, and concentrated in vacuo. The residues were treated with isopropanol giving a white solid which was filtered and dried to give 1-chloro-5-isoquinolinesulphonic acid (1.16 g, 4.77 mmol).

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. temperaturecooled in an ice bath
  3. additionpoured onto ice (70 g)
  4. washwashed with ether
  5. concentrationconcentrated in vacuo
  6. additionThe residues were treated with isopropanol giving a white solid which
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-18bfbfcad1d041708f73a2e4bcd7b63a
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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