4-Methyl-2,6-dinitrobenzoic acid → 3,5-Diamino-p-toluic acid

HRID 2052597Notes

Reaction equation

HRID 2052597 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:16])[CH:7]=[C:8]([N+:13]([O-])=O)[C:9]=1[C:10]([OH:12])=[O:11])([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH3:16])[CH:7]=[C:8]([NH2:13])[C:9]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 120522384-Methyl-2,6-dinitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 570597123,5-Diamino-p-toluic acidYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,5-dinitro-p-toluic acid (10.0 gm.) is dissolved in methanol (300 ml.) and 5% palladium on charcoal (1.0 gm.) added. Reduction is carried out in a Parr apparatus for one hour at 40 psi of hydrogen. The product precipitates and the reaction mixture warmed until solution is complete. The catalyst is removed by filtration, washed with a few cc of methanol and the filtrate cooled to 0°. The product precipitates in fine needles and is collected by filtration, washed with a few ml. of methanol and dried (5.95 gm., 81% yield, m.p. 218°-200° dec.). The thin layer chromatogram (Silica gel, 5% methanol in chloroform) shows the material to be homogeneous.

Workup

  1. customThe product precipitates
  2. temperaturethe reaction mixture warmed until solution
  3. customThe catalyst is removed by filtration
  4. washwashed with a few cc of methanol
  5. temperaturethe filtrate cooled to 0°
  6. customThe product precipitates in fine needles
  7. filtrationis collected by filtration
  8. washwashed with a few ml
  9. dry with materialof methanol and dried (5.95 gm., 81% yield, m.p. 218°-200° dec.)

Sources & evidence

ORD record
ord-22064169cb024366ade9fdf9f23eaecb
Source dataset
uspto-grants-1980_01
Patent number
US04186127

Reaction notes

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