Hydrochloric Acid → 1-(2-Methyl-4-nitrophenyl)cyclopropanecarbonitrile

HRID 2119421Notes

Reaction equation

HRID 2119421 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]#[N:13].Br[CH:15](Br)[CH3:16].[OH-].[Na+].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1([C:12]#[N:13])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 112011,1-DibromoethaneHCID 14798Sodium HydroxideHCID 23441474HCID 23441474, compound

Product 1

HCID 234414811-(2-Methyl-4-nitrophenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of (2-methyl-4-nitrophenyl)acetonitrile (100 mg), benzyltriethylammonium chloride (129 mg), dibromoethane (73.4 μL) and 50% sodium hydroxide solution was heated at 70° C. for 1 hour. After quenching the reaction by the addition of concentrated hydrochloric acid at 0° C., and 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 1-(2-Methyl-4-nitrophenyl)cyclopropane-1-carbonitrile (92.1 mg).

Workup

  1. customAfter quenching
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ea20590417b4acf9d0150a26b213821
Source dataset
uspto-grants-2004_02
Patent number
US06686363B2

Reaction notes

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