1-Fluoro-5-methyl-2,4-dinitrobenzene → 4-Fluoro-6-methylbenzene-1,3-diamine

HRID 483306Notes

Reaction equation

HRID 483306 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-])=O)=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH3:8])[CH:7]=1>C(O)C.[Pd]>[F:1][C:2]1[C:3]([NH2:12])=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 1

HCID 5207051-Fluoro-5-methyl-2,4-dinitrobenzene

Product 1

HCID 178215114-Fluoro-6-methylbenzene-1,3-diamineYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 g (0.01 ml) of 5-fluoro-2,4-dinitrotoluene from Step 1 are hydrated with catalytic amounts of palladium/carbon (10% Pd) in 50 ml absolute ethanol. After the catalyst is removed by filtration, the solvent is distilled off completely and the obtained product is recrystallized from toluene. 0.7 g (50 % of theory) of 5-fluoro-2,4-diaminotoluene is obtained which melts at 112° Celsius accompanied by decomposition.

Workup

  1. customAfter the catalyst is removed by filtration
  2. distillationthe solvent is distilled off completely
  3. customthe obtained product is recrystallized from toluene

Sources & evidence

ORD record
ord-e7daa51d1fca454294474c987dae162f
Source dataset
uspto-grants-1993_07
Patent number
US05224965

Reaction notes

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