Hydrochloric Acid → 8-aminoquinoline-5-sulfonic acid

HRID 1979521Notes

Reaction equation

HRID 1979521 reaction equation
C([NH:4][C:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:7][CH:6]=1)(=O)C.[NH+]1C=CC=CC=1.Cl>O>[NH2:4][C:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20431103HCID 20431103, compound

Product 1

HCID 2780708-aminoquinoline-5-sulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml 1-neck round-bottomed flask fitted with a reflux condenser was placed 25.0 g (0.0724 m) of the pyridinium 8-acetamido-5-quinolinesulfonate and 30 ml water. The slurry was heated to effect solution, 30 ml concentrated hydrochloric acid added and the mixture heated to reflux for 1 hour with stirring. A thick crystalline mass separated during the heating period. The thick slurry was then chilled to 0°-5° C. for several hours, filtered and washed with cold 6N hydrochloric acid and THF. The yield was 11.3 g (70 percent) of product as off-white needles.

Workup

  1. customIn a 250 ml 1-neck round-bottomed flask fitted with a reflux condenser
  2. temperatureThe slurry was heated
  3. additionadded
  4. temperaturethe mixture heated
  5. temperatureto reflux for 1 hour
  6. customA thick crystalline mass separated during the heating period
  7. temperatureThe thick slurry was then chilled to 0°-5° C. for several hours
  8. filtrationfiltered
  9. washwashed with cold 6N hydrochloric acid and THF

Sources & evidence

ORD record
ord-bb9ca487e24b41a1a50c91dabb5f12d0
Source dataset
uspto-grants-1984_11
Patent number
US04481141

Reaction notes

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