Water → HCID 11401556, compound

HRID 1989820Notes

Reaction equation

HRID 1989820 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:13])[C:11]#[N:12].[CH3:14]I.[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([CH3:14])([CH3:13])[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11816413HCID 11816413, compound

Product 1

HCID 11401556HCID 11401556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(2-chloro-4-methoxy-phenyl)propionitrile (19 g, 0.097 mol) and methyliodide (7 mL, 0.11 mol) in dry DMF (100 mL) was flushed with argon for 2 min and cooled to 0° C. Sodium hydride (60% oil susp., 4.4 g, 0.11 mol) was added in small portions. The thick suspension was stirred for another 18 h at 25° C. and then poured into water (300 mL) and extracted with Et2O (3×100 mL). The organic phase was dried (Na2SO4) and the solvent was removed under reduced pressure leaving a yellow oil which was distilled. Bp: 103-106° C./0.06 mbar, clear oil that solidifies on standing. Yield: 17.5 g (83%). GCMS: >99%

Workup

  1. extractionextracted with Et2O (3×100 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure
  4. customleaving a yellow oil which
  5. distillationwas distilled

Sources & evidence

ORD record
ord-26634acade5945c6aa37fec4dfca459f
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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