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

HRID 986667Notes

Reaction equation

HRID 986667 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4]>CO.[Pd]>[CH3:1][C:2]1[C:3]([NH2:4])=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 112982-Methyl-6-nitroaniline

Product 1

HCID 175932,3-Diaminotoluene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.56 (30 m mol) of 2-methyl-6-nitroaniline in 150 ml of methanol was hydrogenated at atmospheric pressure over 0.9 g of 5% Pd/C with Ishii's Catalytic Hydrogenation Apparatus with Magnetic Stirrer Model CHA-M. The catalyst was filtered off. The solvent was evaporated, and the residue was crystallized from petroleum ether to give 3.25 g (88.67%) as gray crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. customThe solvent was evaporated
  3. customthe residue was crystallized from petroleum ether
  4. customto give 3.25 g (88.67%) as gray crystals

Sources & evidence

ORD record
ord-166604b959074423a30b9faf531e36b7
Source dataset
uspto-grants-1987_12
Patent number
US04714764

Reaction notes

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