Water → 4-Chloro-3-methoxy-2-pyridineacetonitrile

HRID 1635089Notes

Reaction equation

HRID 1635089 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]Br)[C:3]=1[O:10][CH3:11].[C-:12]#[N:13].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:12]#[N:13])[C:3]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 18675872HCID 18675872, compound

Product 1

HCID 186758634-Chloro-3-methoxy-2-pyridineacetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-3-methoxy-2-bromomethyl-pyridine (4.69 g) and sodium cyanide (5.11 g) are added to ml of a 1/1 mixture of water and ethanol. The reaction is stirred at 60° C. for 3 hours. The ethanol is evaporated and the residue diluted in water and extracted with methylene chloride. The desired product is obtained by chromatography using hexane/ethyl acetate (9/1) as solvent.

Workup

  1. customThe ethanol is evaporated
  2. additionthe residue diluted in water
  3. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-7a74eb47a6c94082873b70e9a95b1077
Source dataset
uspto-grants-2003_01
Patent number
US06509349B1

Reaction notes

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