Sulfuric Acid → 1H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dione

HRID 2085115Notes

Reaction equation

HRID 2085115 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2.[O:19]=[CH:20][C:21](Cl)(Cl)Cl.Cl.NO.S(=O)(=O)(O)[OH:29]>Cl.C(O)C.O>[C:21]1(=[O:29])[C:10]2=[C:11]3[C:16](=[CH:17][CH:18]=[C:9]2[NH:8][C:20]1=[O:19])[N:15]=[CH:14][CH:13]=[CH:12]3

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 6407ChloralHCID 113736-AminoquinolineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 213070621H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dioneYield 46%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a 1 L flask was added sodium sulfate (0.6 mol) and water (100 mL) and the mixture was stirred until the solids dissolved. To this solution was added a solution of 6-aminoquinoline (0.033 mol) in 1N aqueous hydrochloric acid (50 mL) and ethanol (10 mL). The mixture was stirred and chloral (0.036 mol) was added. To the resulting solution was added a solution of hydroxylamine hydrochloride (0.108 mmol) in water (30 mL). This mixture was then heated to gentle reflux until all the solids dissolved and was then heated for a further 15 min. The flask was removed from the heat and the solution was poured onto ice (500 g) with stirring. The resulting solid was collected by filtration, washed with water and air dried to give N-quinolin-6-yl-2-hydroxyiminoacatamide (94%). To a 1L, 3 necked flask was added concentrated sulfuric acid (100 mL). The acid was stirred and heated to 100 C. N-Quinolin-6-yl-2-hydroxyiminoacatamide (45 mmol) was added slowly and the resulting solution was heated for 1 h. The reaction mixture was carefully poured onto ice/water (750 mL) and stirred for about 1 h. The solids were collected by filtration, washed with water and air dried to give the desired compound, (46%).

Workup

  1. dissolutiondissolved
  2. stirringThe mixture was stirred
  3. temperatureThis mixture was then heated
  4. temperatureto gentle reflux until all the solids
  5. dissolutiondissolved
  6. temperaturewas then heated for a further 15 min
  7. customThe flask was removed from the
  8. temperatureheat
  9. additionthe solution was poured onto ice (500 g)
  10. stirringwith stirring
  11. filtrationThe resulting solid was collected by filtration
  12. washwashed with water and air
  13. customdried
  14. customto give N-quinolin-6-yl-2-hydroxyiminoacatamide (94%)
  15. stirringThe acid was stirred
  16. temperatureheated to 100 C
  17. additionN-Quinolin-6-yl-2-hydroxyiminoacatamide (45 mmol) was added slowly
  18. temperaturethe resulting solution was heated for 1 h
  19. additionThe reaction mixture was carefully poured onto ice/water (750 mL)
  20. stirringstirred for about 1 h
  21. filtrationThe solids were collected by filtration
  22. washwashed with water and air
  23. customdried

Sources & evidence

ORD record
ord-904b6709393d43c3a14e997d794c718a
Source dataset
uspto-grants-2004_04
Patent number
US06720332B2

Reaction notes

Loading…