Sulfuric Acid → (6-Methyl-3-nitropyridin-2-yl)acetonitrile

HRID 728768Notes

Reaction equation

HRID 728768 reaction equation
[N+:1]([C:4]1[C:5]([CH2:25][C:26]#[N:27])=[N:6][C:7]([CH:10](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:8][CH:9]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:10][C:7]1[N:6]=[C:5]([CH2:25][C:26]#[N:27])[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 15009581HCID 15009581, compound

Product 1

HCID 14822074(6-Methyl-3-nitropyridin-2-yl)acetonitrileYield 59.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (3-nitro-6-(dicarbo-t-butoxymethyl)-2-pyridyl)acetonitrile (6.85 g, 18.2 mmol), dioxane (150 mL), and 2M sulfuric acid (25 mL) was heated at reflux for 12 hours. The resulting solution was cooled, neutralized with sodium carbonate, and extracted with ethyl acetate (3×50 mL). These extracts were combined, dried (MgSO4), and evaporated under reduced pressure to yield an oil. This oil was passed through a silica gel filter (approximately 100 g) followed by methylene chloride. This filtrate was evaporated under reduced pressure to afford (6-methyl-3-nitro-2-pyridyl)acetonitrile (1.91 g, 10.8 mmol, 59%) as an off-white solid: mp, 70°-72° C.; IR (KBr)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. temperatureThe resulting solution was cooled
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto yield an oil
  8. filtrationfilter (approximately 100 g)
  9. customThis filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f21b762a112472ea46ac3d9c7c3aa2d
Source dataset
uspto-grants-1991_09
Patent number
US05051412

Reaction notes

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