Benzene, 1-methoxy-3,5-dinitro- → 5-Methoxybenzene-1,3-diamine

HRID 1730684Notes

Reaction equation

HRID 1730684 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([O:13][CH3:14])[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

4

Reactant 1

HCID 79231Benzene, 1-methoxy-3,5-dinitro-

Product 1

HCID 128973335-Methoxybenzene-1,3-diamineYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,5-Dinitroanisole (20 gm.) is suspended in methanol (250 ml.) and 5% palladium on charcoal (2.0 gm.) added. Reduction is carried out in a Parr apparatus for one hour. The solution is filtered with suction and the catalyst washed with a few cc of methanol. Removal of the methanol gives a clear brown glass which crystallized on standing. Extraction with boiling benzene (250 ml.) and treatment with Darco gives white needles (8.7 gm., m.p. 79°-80°, 63% yield).

Workup

  1. filtrationThe solution is filtered with suction
  2. washthe catalyst washed with a few cc of methanol
  3. customRemoval of the methanol
  4. customgives a clear brown glass which
  5. customcrystallized
  6. extractionExtraction with boiling benzene (250 ml.) and treatment with Darco
  7. customgives white needles (8.7 gm., m.p. 79°-80°, 63% yield)

Sources & evidence

ORD record
ord-917b3319450040de85a518080d3cdbe7
Source dataset
uspto-grants-1976_11
Patent number
US03993679

Reaction notes

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