2-Methyl-6-nitroaniline → 2,3-Diaminotoluene

HRID 1648286Notes

Reaction equation

HRID 1648286 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4].[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[C:3]=1[NH2:4]

Participants

5

Reactant 2

HCID 112982-Methyl-6-nitroanilineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 175932,3-DiaminotolueneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-6-nitroaniline (15.2 g, 0.1 mol) was dissolved by heating in ethanol (150 mL). The solution was cooled, 10% palladium on carbon (1.0 g) was added and the solution was hydrogenated (50 lb initial hydrogen pressure) until uptake of hydrogen ceased (1 hour). The catalyst was filtered off and the ethanol was removed under reduced pressure to give 11.9 g (98%) of 3-methyl-l,2-benzenediamine as a solid which was used without purification.

Workup

  1. temperatureThe solution was cooled
  2. custom(1 hour)
  3. filtrationThe catalyst was filtered off
  4. customthe ethanol was removed under reduced pressure

Sources & evidence

ORD record
ord-4dbf6f99881a4439be56e71c4142b0e8
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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