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

HRID 1730681Notes

Reaction equation

HRID 1730681 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 1 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. 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°-220° dec.)

Sources & evidence

ORD record
ord-36fb8e0e7e3b461aa71f6d905519bf46
Source dataset
uspto-grants-1976_11
Patent number
US03993679

Reaction notes

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