Potassium Cyanide → 5-Chloro-6-ethyl-pyridin-3-yl-acetonitrile

HRID 900972Notes

Reaction equation

HRID 900972 reaction equation
[Cl:1][C:2]1[C:3]([CH2:10][CH3:11])=[N:4][CH:5]=[C:6]([CH2:8]Cl)[CH:7]=1.[C-:12]#[N:13].[K+]>CN(C)C=O.O.[Na+].[Cl-]>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][C:12]#[N:13])[CH:5]=[N:4][C:3]=1[CH2:10][CH3:11]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 596988003-Chloro-5-chloromethyl-2-ethyl-pyridine

Product 1

HCID 596987915-Chloro-6-ethyl-pyridin-3-yl-acetonitrileYield 90.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-5-chloromethyl-2-ethyl-pyridine (4.03 g, 21 mmol) in dimethylformamide (26 mL, 0.8 M) is cooled to 0° C. and treated with a solution of potassium cyanide (1.48 g, 22.7 mmol) in water (10 mL). After 4 h, the solution is diluted with 50% aq NaCl and extracted with ethyl acetate. The organic extracts are washed with sat'd aq lithium chloride and purified by MPLC (30-90% ethyl acetate in heptane) to give 5-chloro-6-ethyl-pyridin-3-yl-acetonitrile as a light brown oil (3.42 g, 90%): Rf 0.29 (30% ethyl acetate in n-heptane), 1H NMR (CDCl3, 300 MHz) δ 8.38 (br s, 1 H), 7.67 (br s, 1 H), 3.74 (s, 2 H), 2.97 (q, J=7.5 Hz, 2 H), 1.30 (t, J=7.5 Hz, 3 H) ESI-LCMS m/z calcd for C9H9ClN2: 180.0; found 181.0 (M+1)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts are washed with sat'd aq lithium chloride
  3. custompurified by MPLC (30-90% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-1c3e8593664b41beba8694df014a6402
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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