Pyridine → 2,6-Dichloropyridine-3-carbonitrile

HRID 1823503Notes

Reaction equation

HRID 1823503 reaction equation
[Cl:1][C:2]1[C:7](NC(=O)C)=[CH:6][CH:5]=[C:4]([Cl:12])[N:3]=1.[N:13]1C=CC=C[CH:14]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[C:7]([C:14]#[N:13])=[CH:6][CH:5]=[C:4]([Cl:12])[N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 12611966HCID 12611966, compound

Product 1

HCID 126055382,6-Dichloropyridine-3-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,6-dichloro-3-acetamidopyridine (6.3 g, 55% pure) and pyridine (4.93 ml, 61 mmole) in dichloromethane (100 ml), trifluoroacetic anhydride (4.23 ml, 30 mmole) was added. The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with 85% hexane:15% ethyl acetate to give a pale yellow product (1.77 g, 90%).

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by flash chromatography
  4. washeluting with 85% hexane

Sources & evidence

ORD record
ord-402a566656ed474ab6933cdc14fa9485
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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