Isonicotinic acid, 2-chloro-3-cyano-6-methyl-, ethyl ester → HCID 89875540, compound

HRID 715244Notes

Reaction equation

HRID 715244 reaction equation
[Cl:1][C:2]1[C:3]([C:14]#[N:15])=[C:4]([CH:10]=[C:11]([CH3:13])[N:12]=1)[C:5](OCC)=[O:6]>CCO.[Ni]>[Cl:1][C:2]1[C:3]2[CH2:14][NH:15][C:5](=[O:6])[C:4]=2[CH:10]=[C:11]([CH3:13])[N:12]=1

Participants

4

Reactant 1

HCID 142408Isonicotinic acid, 2-chloro-3-cyano-6-methyl-, ethyl ester

Product 1

HCID 89875540HCID 89875540, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-chloro-3-cyano-6-methylisonicotinate (1.0 g, 4.5 mmol) in EtOH (14.8 mL) is added Raney nickel (100 mg, RANEY 2800 NICKEL), and the mixture is stirred at 60° C. under hydrogen atmosphere for 2 days. After cooling to rt, the reaction mixture is filtered through a pad of Celite™. The filtrate is concentrated, and the residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:1), and the collecting sample is recrystallized from THF/n-hexane to give 91 mg (11% yield) of the title compound as white solid.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe reaction mixture is filtered through a pad of Celite™
  3. concentrationThe filtrate is concentrated
  4. customthe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:1)
  5. customthe collecting sample is recrystallized from THF/n-hexane

Sources & evidence

ORD record
ord-196f8dad137b40fd88e4e10957055c8a
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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