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

HRID 1258576

反応式

HRID 1258576 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-349f004a71d94e8d92cdcdcfb64a611c
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

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