Water → 5-Methylnicotinonitrile

HRID 52356Notes

Reaction equation

HRID 52356 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)Cl>[C:7]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[CH:10]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 655605-Methylnicotinamide

Product 1

HCID 6378385-MethylnicotinonitrileYield 100,918.297%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-methyl-nicotinamide from step 2 (10.5 g, 0.077 mmol) in triethylamine (23.3 g, 0.23 mmol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mmol) rapidly at 0° C. The reaction was completed after a few minutes. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated to give 9.18 g of 3-cyano-5-methylpyridine crude, which was used in the next step without purification.

Workup

  1. waitThe reaction was completed after a few minutes
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f04c44335a40448cba0cf4f445f9f28e
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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