2-Chloro-4-iodo-nicotinic acid methyl ester → Methyl 2-chloro-4-cyanonicotinate

HRID 711457Notes

Reaction equation

HRID 711457 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8](I)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([Cu])#[N:14]>CC(N(C)C)=O>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 108515652-Chloro-4-iodo-nicotinic acid methyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 58317566Methyl 2-chloro-4-cyanonicotinateYield 34.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of methyl 2-chloro-4-iodonicotinate (3.20 g, 10.76 mmol) and cyanocopper (0.963 g, 10.76 mmol) in DMA (40 mL) was stirred at 140° C. overnight. Following reaction, the mixture was filtered through Celite and the filtrate was diluted with H2O and EtOAc. The aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1) to give the title compound as a white solid (730 mg, 34.5%). 1H NMR (500 MHz, CDCl3) δ ppm 4.07 (s, 3H), 7.57 (d, J=5.37 Hz, 1H), 8.66 (d, J=4.88 Hz, 1H).

Workup

  1. customreaction
  2. filtrationthe mixture was filtered through Celite
  3. additionthe filtrate was diluted with H2O and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by chromatography on SiO2 (Hexane/EtOAc=10/1)

Sources & evidence

ORD record
ord-8cb5dc0df4a14674886413123041f5b2
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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