6-(Bromomethyl)-2-methylquinoline → 2-(2-Methylquinolin-6-ylmethyl)-isoindole-1,3-dione

HRID 1173977

Reaction equation

HRID 1173977 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH:7]=[CH:6]2.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C=O)C>[CH3:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][N:18]3[C:14](=[O:24])[C:15]4[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:17]3=[O:19])[CH:4]=2)[N:9]=1

Participants

4

Reactant 2

HCID 27954806-(Bromomethyl)-2-methylquinolineHCID 24194345Phthalimide potassium salt

Product 1

HCID 230791882-(2-Methylquinolin-6-ylmethyl)-isoindole-1,3-dioneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (421.7 mg) obtained in Example 119-1 was dissolved in anhydrous DMF (12.6 ml) and added with potassium phthalimide (663.1 mg), followed by stirring at room temperature for 2 hours. After the reaction, the solvent was distilled off and the residue was then added with water. The mixture was extracted with chloroform and the extract was dried with magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (536.0 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was then added with water
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe extract was dried with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-e0051928026e48a7ae95d4550f6edc0f
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Linked notes

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