3,5-Dichloroisonicotinamide → 3,5-Dichloropyridine-4-carbonitrile

HRID 1159447Notes

Reaction equation

HRID 1159447 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([NH2:6])=O>O=P(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]#[N:6]

Participants

3

Reactant 1

HCID 28029113,5-Dichloroisonicotinamide

Product 1

HCID 111375993,5-Dichloropyridine-4-carbonitrileYield 63.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

The product from Example 1A (2.1 g, 11 mmol) in POCl3 (25 mL) was stirred at reflux overnight, allowed to cool to room temperature, poured onto ice, and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to give 1.2 g of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 8.96 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. additionpoured onto ice
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-57e03497db9745c59d3bd42fbe774909
Source dataset
uspto-grants-2010_10
Patent number
US07812166B2

Reaction notes

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