Hydrochloric Acid → HCID 71103879, compound

HRID 2119420Notes

Reaction equation

HRID 2119420 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[CH3:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1F.Cl>CS(C)=O>[CH3:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[CH:5]([C:3]#[N:4])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 71103879HCID 71103879, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (60% oil dispersion, 6.13 g) in dimethyl sulfoxide (100 mL) was added ethyl cyanoacetate (18.0 g) at 0° C., and the mixture was stirred at room temperature for 2 hours. 2-Methyl-4-nitrofluorobenzene (9.15 g) was added to the mixture, and the resulting solution was stirred at room temperature for 12 hours. After quenching the reaction by the addition of 6 N hydrochloric acid at 0° C., and the mixture was extracted with ether. The ethereal solution was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo to give ethyl (2-methyl-4-nitrophenyl)cyanoacetate. A solution of crude ethyl (2-methyl-4-nitrophenyl)cyanoacetate thus obtained in dioxane (200 mL) and 6 N hydrochloric acid (200 mL) was heated at 100° C. for 12 hours. After dilution of the mixture with water and sodium chloride, the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=2:1) of the residue gave (2-methyl-4-nitrophenyl)acetonitrile (5.32 g).

Workup

  1. stirringthe resulting solution was stirred at room temperature for 12 hours
  2. customAfter quenching
  3. customthe reaction
  4. extractionthe mixture was extracted with ether
  5. washThe ethereal solution was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adfab7df12f1463893dbccafc81199ed
Source dataset
uspto-grants-2004_02
Patent number
US06686363B2

Reaction notes

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