6-Chloromethyl-2-cyanopyridine → 6-Phthalimidomethyl-2-pyridinecarbonitrile

HRID 2379792Notes

Reaction equation

HRID 2379792 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][CH: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)C=O>[C:11]1(=[O:21])[N:15]([CH2:2][C:3]2[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][CH:4]=2)[C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12

Participants

4

Reactant 2

HCID 103518756-Chloromethyl-2-cyanopyridineHCID 24194345Phthalimide potassium salt

Product 1

HCID 100383916-Phthalimidomethyl-2-pyridinecarbonitrileYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloromethyl-2-pyridinecarbonitrile (2.75 g) and potassium phthalimide (3.35 g) in N,N-dimethylformamide (27.5 ml) was stirred at ambient temperature for 4 hours. After the solvent was evaporated in vacuo, water (50 ml) was added to the residue and the resulting precipitate was collected by filtration to give 6-phthalimidomethyl-2-pyridinecarbonitrile (4.60 g).

Workup

  1. customAfter the solvent was evaporated in vacuo, water (50 ml)
  2. additionwas added to the residue
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-41b7f1a76b7a4daebc2c74668a26b625
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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