1-Chloro-4-methoxy-5-methyl-2-nitrobenzene → HCID 57687200, compound

HRID 1443468Notes

Reaction equation

HRID 1443468 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Cu](C#N)[C:15]#[N:16]>C(OCC)(=O)C>[CH3:10][O:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:15]#[N:16])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

4

Reactant 2

HCID 137856681-Chloro-4-methoxy-5-methyl-2-nitrobenzeneHCID 178418260HCID 178418260, compound

Product 1

HCID 57687200HCID 57687200, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture compound 108 (20 g, 100 mmol) and copper cyanide (11.25 g, 125 mmol) in n-methyl-pyrrolidone-2 (60 ml) was stirred for 20 h at 140-150° C. The mixture was diluted with ethyl acetate filtered and washed four times with water. The organic phase was dried with sodium sulphate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with hexane-ethyl acetate which gave the title compound (8 g, 41%).

Workup

  1. filtrationfiltered
  2. washwashed four times with water
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluted with hexane-ethyl acetate which

Sources & evidence

ORD record
ord-73b81c50cf6b4509bbd4a1a352413915
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

Loading…