Dimethylformamide → 5-Cyanomethyl-2,6-dimethyl-pyridin-3-yl-acetonitrile

HRID 900966Notes

Reaction equation

HRID 900966 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:12])=[N:5][C:6]([CH3:11])=[C:7]([CH2:9]Cl)[CH:8]=1.[C-:13]#[N:14].[K+].C[N:17]([CH3:20])C=O>O>[C:13]([CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][C:20]#[N:17])[C:6]([CH3:11])=[N:5][C:4]=1[CH3:12])#[N:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 123681323,5-Bis-chloromethyl-2,6-dimethyl-pyridine

Product 1

HCID 689391815-Cyanomethyl-2,6-dimethyl-pyridin-3-yl-acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3,5-bis-chloromethyl-2,6-dimethyl-pyridine (18.0 g, 88.2 mmol) in dimethylformamide (110 mL, 0.8 M) is cooled to 0° C. and treated with a solution of potassium cyanide (12.4 g, 190 mmol) in water (35 mL). The cooling bath is removed, and after 4 h, ice-cooled H2O (600 mL) is added. The resulting solids are filtered, washed with ice-cooled water (100 mL) and recrystallized from H2O to provide 5-cyanomethyl-2,6-dimethyl-pyridin-3-yl-acetonitrile as light brown flakes (10.9 g, 67%): mp 65-67° C.; Rf 0.23 (20% n-heptane in ethyl acetate); 1H NMR (CDCl3, 300 MHz) δ 7.61 (s, 1 H), 3.69 (s, 4 H), 2.56 (s, 6 H); ESI-LCMS m/z calcd for C11H11N3: 185.1; found 186.0 (M+1)+. Anal. Calcd for C11H11N3.0.15H2O: C, 70.30; H, 6.06; N, 22.36. Found: C, 70.44; H, 6.01; N, 22.13.

Workup

  1. customThe cooling bath is removed
  2. temperatureice-cooled H2O (600 mL)
  3. additionis added
  4. filtrationThe resulting solids are filtered
  5. washwashed with ice-
  6. temperaturecooled water (100 mL)
  7. customrecrystallized from H2O

Sources & evidence

ORD record
ord-f217ca6b509f43d39dffd60e6f01f116
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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