Diethyl Ether → (2-Methyl-3-nitrophenyl)acetonitrile

HRID 618232Notes

Reaction equation

HRID 618232 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:12].[C-:13]#[N:14].[Na+].[I-].[Na+].CCOCC>CN(C)C=O>[CH3:12][C:4]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:13]#[N:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 108947alpha-Chloro-2-methyl-3-nitrotoluene

Product 1

HCID 13530896(2-Methyl-3-nitrophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Chloromethyl-2-methyl-3-nitro-benzene (25g) was dissolved in 125 ml of N,N-dimethylformamide. To this mixture was added 10.89 g of sodium cyanide (Mallinckrodt, Paris, Ky.) and 0.4 g of sodium iodide (Mallinckrodt) and the heterogeneous mixture was heated to 80° C. for 21 hr. The reaction mixture was cooled to room temperature, poured into ether, washed several times with water, dried, and evaporated. The residue was purified by flash chromatography on silica gel eluting with dichloromethane, giving 16.83 g of (2-methyl-3-nitro-phenyl)-acetonitrile as a cream solid. ##STR103##

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed several times with water
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-75a6e06911574b948b899f047e589356
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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