Dimethylformamide → HCID 15527620, compound

HRID 901883Notes

Reaction equation

HRID 901883 reaction equation
F[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:5]([C:6]#[N:7])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.CN(C)[CH:18]=[O:19].C[O-].[Na+]>CO>[CH3:18][O:19][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:5]([C:6]#[N:7])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 18444517HCID 18444517, compound

Product 1

HCID 15527620HCID 15527620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To 1.92 g (9.11 mmol) of 4-fluoro-2,6-dinitrobenzonitrile dissolved in 20 mL methanol and 3 mL dimethylformamide at 0° C. was added 1.87 mL (1 eq., 4.87 M in methanol) sodium methoxide over 1 hour. The mixture was stirred an additional hour at 0° C., partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography, eluting with ethyl acetate/hexanes, provided 1.32 g of 4-methoxy-2,6-dinitrobenzonitrile.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washColumn chromatography, eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-407089da73f945ada5118db0aa199dbd
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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