2-Cyanobenzeneacetonitrile → HCID 15426261, compound

HRID 2404400Notes

Reaction equation

HRID 2404400 reaction equation
[CH3:1][Li].[C:3]([CH2:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9])#[N:4]>C1COCC1>[CH3:1][C:8]1[C:7]2[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:3]([NH2:4])[N:9]=1

Participants

4

Reactant 2

HCID 773682-CyanobenzeneacetonitrileHCID 178418348HCID 178418348, compound

Product 1

HCID 15426261HCID 15426261, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a dry flask under N2 containing methyllithium (13 mL, 21 mmol) in THF (40 mL) at 0° C. was added a solution of 2-(cyanomethyl)benzonitrile (1.00 g, 7.03 mmol) in THF (20 mL) dropwise. After 10 minutes the ice bath was removed and the mixture was allowed to warm to ambient temperature. The mixture was quenched with saturated aqueous NH4Cl and then concentrated. The mixture was extracted twice with CH2Cl2, and the combined organic extracts were washed with brine and dried (Na2SO4). Purification by chromatography (SiO2, 10% acetone/hexanes) afforded the title compound 0.71 g (79% yield). MS (ESI) m/z 159 (M+H)+.

Workup

  1. customAfter 10 minutes the ice bath was removed
  2. customThe mixture was quenched with saturated aqueous NH4Cl
  3. concentrationconcentrated
  4. extractionThe mixture was extracted twice with CH2Cl2
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customPurification by chromatography (SiO2, 10% acetone/hexanes)

Sources & evidence

ORD record
ord-e5379f9dd07642be997077f8afe92fba
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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