Dimethylformamide → Ethyl 5-chloro-6-cyanonicotinate

HRID 1479532Notes

Reaction equation

HRID 1479532 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N>[Cl:1][C:2]1[C:3]([C:14]#[N:15])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 66875248Ethyl 5-chloro-6-cyanonicotinate

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 5,6-dichloronicotinate (1 eq), zinc cyanide (0.75 eq) and tetrakis(triphenyl-phosphine)palladium (0.10 eq.) in DMF (0.3 M) was degassed and then heated at 100° C. for 3 hours. Solvent was removed en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give ethyl 5-chloro-6-cyanonicotinate as a white solid.

Workup

  1. customSolvent was removed en vaccuo
  2. customto obtain a crude residue
  3. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-cf1dc702b909494fa6510a0685d1470f
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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