7-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione → HCID 178515077, compound

HRID 323638Notes

Reaction equation

HRID 323638 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:28])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([O:25]C)[CH:18]=4)[N:13]=[C:12]([OH:27])[C:8]=3[NH:9][C:10]=2[CH:11]=1>Br>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:28])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([OH:25])[CH:18]=4)[N:13]=[C:12]([OH:27])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

3

Reactant 1

HCID 1784920847-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione

Product 1

HCID 178515077HCID 178515077, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

7-Chloro-4-hydroxy-2-(3,4-dimethoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (1.00 g, 2.50 mM) was refluxed in 48% HBr (40 mL) for 6 hours to give an orange suspension. Heat was removed and the suspension was filtered while still warm. The collected solids were washed with water and then ether to give the crude product (0.94 g) as a yellow powder. This material was recrystallized from refluxing methanol (600 mL) to give the title compound (0.63 g, 68%) as a yellow powder, mp 269-272° C.; MS(CI): 372 (M+H).

Workup

  1. customto give an orange suspension
  2. temperatureHeat
  3. customwas removed
  4. filtrationthe suspension was filtered
  5. temperaturewhile still warm
  6. washThe collected solids were washed with water
  7. customether to give the crude product (0.94 g) as a yellow powder
  8. customThis material was recrystallized
  9. temperaturefrom refluxing methanol (600 mL)

Sources & evidence

ORD record
ord-b4f3b85f3e034ba1b4a26eda892c0740
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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