8-Aminoquinoline → HCID 21973698, compound

HRID 11854

Reaction equation

HRID 11854 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>CN(C=O)C>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 113598-AminoquinolineHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 21973698HCID 21973698, compoundYield 172.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Aminoquinoline (1.26 g) was dissolved in DMF (20 ml), and potassium carbonate (1.2 g) and methyl 4-bromomethylbenzoate (1.0 g) were added. After stirring for 20 hours, the reaction solution was concentrated. The resulting residue was diluted with chloroform and water was added. The mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain the title compound (2.20 g) as a yellow syrup.

Workup

  1. concentrationthe reaction solution was concentrated
  2. additionThe resulting residue was diluted with chloroform and water
  3. additionwas added
  4. extractionThe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e776eb67f904408b46f21893414ce16
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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