2,6-Bis(chloromethyl)pyridine → 1H-Isoindole-1,3(2H)-dione, 2-[[6-(chloromethyl)-2-pyridinyl]methyl]-

HRID 1258576

Reaction equation

HRID 1258576 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Cl:10])[N:4]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C=O)C>[Cl:10][CH2:9][C:5]1[N:4]=[C:3]([CH2:2][N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 3166542,6-Bis(chloromethyl)pyridineHCID 24194345Phthalimide potassium salt

Product 1

HCID 666711941H-Isoindole-1,3(2H)-dione, 2-[[6-(chloromethyl)-2-pyridinyl]methyl]-Yield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-bis(chloromethyl)pyridine (20 g, 113.6 mmol, 1 eq.) in 250 ml of DMF was added potassium phthalimide (21.04 g, 113.6 mmol, 1 eq.). The reaction was stirred at r.t. overnight then the solvent was evaporated and the residue taken in EtOAc. The insolubles were removed by filtration and the filtrate washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The resulting white solid was recrystallised from IPE/EtOAc (1/1) to give 2-{[6-(chloromethyl)pyridin-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (22.34 g, 68% yield) as a white solid.

Workup

  1. customthe solvent was evaporated
  2. customThe insolubles were removed by filtration
  3. washthe filtrate washed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting white solid was recrystallised from IPE/EtOAc (1/1)

Sources & evidence

ORD record
ord-349f004a71d94e8d92cdcdcfb64a611c
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Linked notes

Loading…