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

HRID 236938Notes

Reaction equation

HRID 236938 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>[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

4

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 1

HCID 887MethanolSolvent

Procedure

3,5-dinitro-p-toluic acid (10.0 gm.) is dissolved in methanol (300 ml.) and 5% palledium 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°-220° dec.). The thin layer chromatogram (Silica gel, 5% methanol in chloroform) shows the material to be homogeneous.

Workup

  1. addition5% palledium on charcoal (1.0 gm.) added
  2. customThe product precipitates
  3. temperaturethe reaction mixture warmed until solution
  4. customThe catalyst is removed by filtration
  5. washwashed with a few cc of methanol
  6. temperaturethe filtrate cooled to 0°
  7. customThe product precipitates in fine needles
  8. filtrationis collected by filtration
  9. washwashed with a few ml
  10. dry with materialof methanol and dried (5.95 gm., 81% yield, m.p. 218°-220° dec.)

Sources & evidence

ORD record
ord-8b3183a73a4c44c882a13eb5c320912e
Source dataset
uspto-grants-1979_06
Patent number
US04159278

Reaction notes

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