Hydrochloric Acid → HCID 178428979, compound

HRID 323644

Reaction equation

HRID 323644 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:27])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=4[CH3:25])[N:13]=[C:12]([OH:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1.O.[OH-].OCC[N+](C)(C)C.Cl>CS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:27])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=4[CH3:25])[N:13]=[C:12]([OH:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 31255Choline, hydroxideHCID 178492085HCID 178492085, compound

Product 1

HCID 178428979HCID 178428979, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
150 °C

Procedure

7-Chloro-4-hydroxy-2-(4-methoxy-2-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (1.00 g, 2.61 mM) was stirred in methanesulfonic acid (10 mL) to give a brown solution. This solution was heated to 150° C. for 3 hours and cooled to room temperature. The cooled solution was added dropwise to water (50 mL) with stirring to give a grey suspension which was stirred for 20 hours and filtered. The collected solids were washed with water and then suspended in water (50 mL). To this suspension was added choline hydroxide solution (2 mL, 45 wt % in methanol) which dissolved the solids to give a brown solution. This solution was heated to reflux for 1 hour, additional choline hydroxide solution (2 mL) was added and the solution was heated to reflux for 3 hours. The solution was cooled to room temperature and acidified to pH=1 with 1N HCl to give a brown suspension. The suspension was filtered and the collected solids were washed with water to give a brown solid. Several recrystallizations from hot methanol gave the title compound as an off-white powder (0.35 g, 36%), mp 287° C. (decomp.); MS(CI): 370.

Workup

  1. customto give a brown solution
  2. temperaturecooled to room temperature
  3. customto give a grey suspension which
  4. stirringwas stirred for 20 hours
  5. filtrationfiltered
  6. washThe collected solids were washed with water
  7. additionTo this suspension was added choline hydroxide solution (2 mL, 45 wt % in methanol) which
  8. dissolutiondissolved the solids
  9. customto give a brown solution
  10. temperatureThis solution was heated
  11. temperatureto reflux for 1 hour
  12. temperaturethe solution was heated
  13. temperatureto reflux for 3 hours
  14. temperatureThe solution was cooled to room temperature
  15. customto give a brown suspension
  16. filtrationThe suspension was filtered
  17. washthe collected solids were washed with water
  18. customto give a brown solid
  19. customSeveral recrystallizations from hot methanol

Sources & evidence

ORD record
ord-ad1b830684e74143912fa4ee05f4db91
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Linked notes

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