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

HRID 327443Notes

Reaction equation

HRID 327443 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-1,2-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-58fef6f3936b458ab67901226e08d0fd
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

Loading…