Sodium Methoxide → HCID 23278998, compound

HRID 1019091Notes

Reaction equation

HRID 1019091 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[C:7]([CH3:15])[C:6]=1[N+:16]([O-:18])=[O:17])(=O)C.C[O-].[Na+]>CO>[CH3:15][C:7]1[C:6]([N+:16]([O-:18])=[O:17])=[C:5]([CH:10]=[C:9]([CH3:11])[C:8]=1[N+:12]([O-:14])=[O:13])[NH2:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 17372772HCID 17372772, compound

Product 1

HCID 23278998HCID 23278998, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-acetyl-3,5-dimethyl-2,4-dinitroaniline (14.6 g, 57 mmol) and sodium methoxide (25 wt % solution in methanol) (26 mL) and methanol (200 mL) is heated to reflux for 90 minutes. The mixture is rotary evaporated and the residue is partitioned between water and chloroform. The organic layer is dried (magnesium sulfate) and rotary evaporated. The residue is purified by flash chromatography on silica gel (25% ethyl acetateihexane) to afford 3,5-dimethyl-2,4-dinitroaniline (8.0 g) as an orange solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 90 minutes
  3. customThe mixture is rotary evaporated
  4. customthe residue is partitioned between water and chloroform
  5. dry with materialThe organic layer is dried (magnesium sulfate) and rotary evaporated
  6. customThe residue is purified by flash chromatography on silica gel (25% ethyl acetateihexane)

Sources & evidence

ORD record
ord-57a13d9da6b2411db3818176207001cb
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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