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

HRID 1258576

반응식

HRID 1258576 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-349f004a71d94e8d92cdcdcfb64a611c
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

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