Diethyl Ether → HCID 178492268, compound

HRID 323642Notes

Reaction equation

HRID 323642 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.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1.CCOCC>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][NH:30][C:27]4[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=4)[N:5]=[C:6]([OH:21])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7732P-AnisidineHCID 178515080HCID 178515080, compound

Product 1

HCID 178492268HCID 178492268, compoundYield 60%

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 (1.00 g, 2.7 mM, prepared in Example 4a. and p-anisidine (1.33 g, 10.8 mM) were stirred and heated to reflux in DMF (20 mL) for 1.5 hours to give a brown solution. The solution was cooled to room temperature and ether (80 mL) was added to give a dark suspension. The suspension was stirred for two hours and filtered. The collected solids were washed with ether (150 mL) to give the title compound as a tan powder (1.17 g, 60%), mp 239-241° C.; MS(CI):413.

Workup

  1. temperatureheated
  2. customto give a brown solution
  3. customto give a dark suspension
  4. filtrationfiltered
  5. washThe collected solids were washed with ether (150 mL)

Sources & evidence

ORD record
ord-88823fa93cb64a819b64e968bc80d491
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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