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

HRID 515992Notes

Reaction equation

HRID 515992 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, 3 H), 7.57 (d, J=5.37 Hz, 1 H), 8.66 (d, J=4.88 Hz, 1 H).

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-dd8bf3c260ad425a833911aaa6c52b2e
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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