Methyl 2,6-dinitrobenzoate → Methyl 2,6-diaminobenzoate

HRID 372252

Reaction equation

HRID 372252 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O>CO.[Pd].C(Cl)(Cl)Cl>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 1

HCID 333850Methyl 2,6-dinitrobenzoate

Product 1

HCID 12402975Methyl 2,6-diaminobenzoateYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

Methyl 2,6-dinitrobenzoate (15.0 gm.) is suspended in methanol (500 ml.) and 5% palladium on charcoal (1.5 gm.) added. Reduction is carried out on a Parr apparatus for two hours. The solution is filtered with suction and the catalyst washed with a few ml. of methanol. Removal of the methanol gives a brown crystalline product. Extraction with chloroform (50 ml.) and treatment with Darco® gives the product (10.9 gm. 96% yield, m.p. 78°-79.5°). The thin layer chromatogram (Silica gel, 3% methanol in chloroform) shows the material to be homogeneous.

Workup

  1. filtrationThe solution is filtered with suction
  2. washthe catalyst washed with a few ml
  3. customRemoval of the methanol
  4. customgives a brown crystalline product
  5. extractionExtraction with chloroform (50 ml.) and treatment with Darco®
  6. customgives the product (10.9 gm. 96% yield, m.p. 78°-79.5°)

Sources & evidence

ORD record
ord-2ac40c00ecea44bfba7bab7394397a1c
Source dataset
uspto-grants-1978_05
Patent number
US04089973

Linked notes

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