Water → 2-Methylpyridine-3-carbonitrile

HRID 1352996Notes

Reaction equation

HRID 1352996 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C(Cl)Cl>[C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 122437052-Methylnicotinamide

Product 1

HCID 47383082-Methylpyridine-3-carbonitrileYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0° C. The reaction was complete after a few minutes at this temperature. 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 and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2-methylpyridine as a pale yellow solid (75%): mp(DSC) 56–58° C.

Workup

  1. waitThe reaction was complete after a few minutes at this temperature
  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
  7. customthe residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record
ord-b4a987bb4506433490d555a5f18e995e
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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