Hydrochloric Acid → HCID 178515009, compound

HRID 323608Notes

Reaction equation

HRID 323608 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:17](=[O:18])[C:16]2[C:15](=[O:19])[C:14]3[CH:13]=[CH:12][C:11]([Cl:20])=[CH:10][C:9]=3[NH:8][C:7]=2[C:6]([OH:21])=[N:5]1.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K].Cl>CN(C=O)C>[Cl:20][C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:19])[C:16]3[C:17](=[O:18])[N:4]([CH2:3][CH2:2][N:26]4[C:25](=[O:27])[C:24]5=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]5[C:22]4=[O:32])[N:5]=[C:6]([OH:21])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24194345Phthalimide potassium saltHCID 178515080HCID 178515080, compound

Product 1

HCID 178515009HCID 178515009, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Bromoethyl)-7-chloro-4-hydroxy-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (5.00 g, 13.50 mM) and potassium phthalimide (10.50 g, 56.70 mM) were stirred and refluxed in DMF (100 mL) for 22 hours. The cooled yellow suspension was poured into dilute hydrochloric acid (1N, 1.0 L) with good stirring. A white precipitate formed and was collected. This solid was resuspended in aqueous methanol (50%, 1.0 L) and stirred/sonicated to give a fine white suspension. Filtration and resuspension in methanol (0.25 L) gave a free-flowing white suspension after sonication and brief warming. The solids were finally collected and washed with methanol to give the title compound (4.65 g, 79%) as a white powder, mp 349-352° C.; MS(CI): 437 (M+H).

Workup

  1. customA white precipitate formed
  2. customwas collected
  3. customstirred/sonicated
  4. customto give a fine white suspension
  5. filtrationFiltration and resuspension in methanol (0.25 L)
  6. customgave a free-flowing white suspension
  7. customafter sonication and brief warming
  8. customThe solids were finally collected
  9. washwashed with methanol

Sources & evidence

ORD record
ord-100eeb15df884c29ad60df510692c664
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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