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

HRID 1600050Notes

Reaction equation

HRID 1600050 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 washedwith 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. customether to give the crude product (0.94 g) as a yellow powder
  7. customThis material was recrystallized
  8. temperaturefrom refluxing methanol (600 mL)

Sources & evidence

ORD record
ord-0b14d3d2e42c48228110b38140676ad8
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

Loading…