Ethanol → HCID 44549262, compound

HRID 1512978Notes

Reaction equation

HRID 1512978 reaction equation
S(=O)(=O)(O)[OH:2].[C:6]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=1)#N.[CH2:18]([OH:20])[CH3:19]>>[CH3:14][C:12]1[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=[C:8]([C:6]([O:20][CH2:18][CH3:19])=[O:2])[CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 230001714-Methyl-5-nitropyridine-2-carbonitrile

Product 1

HCID 44549262HCID 44549262, compound

Conditions

Temperature
120 °C

Procedure

To concentrated sulfuric acid (45 mL) was added ethanol (100 mL) under ice-cooling, followed by adding 2-cyano-4-methyl-5-nitropyridine (3.54 g), and the reaction vessel was equipped with a reflux condenser, and the mixture was stirred at 120° C. for 2 hours. The reaction mixture was cooled to room temperature. The reaction mixture was poured into ice, and the resulting mixture was extracted with diethyl ether. The water layer was extracted with methylene chloride. The extracts were combined, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (3.23 g).

Workup

  1. temperaturecooling
  2. customthe reaction vessel was equipped with a reflux condenser
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionThe reaction mixture was poured into ice
  5. extractionthe resulting mixture was extracted with diethyl ether
  6. extractionThe water layer was extracted with methylene chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-ef4817d0cefb4cefa1413944faa800a3
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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