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

HRID 1862162Notes

Reaction equation

HRID 1862162 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N+:12]([O-])=O>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][C:3]=1[NH2:12]

Participants

4

Reactant 1

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

Product 1

HCID 178215114-Fluoro-6-methylbenzene-1,3-diamineYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-fluoro-5-methyl-2,4-dinitro-benzene (1.0 g, 5 mmol) and 10% Pd/C (200 mg) in MeOH (20 ml) was hydrogenated at 23° C. for 24 h. The reaction mixture was filtered through celite and concentrated. Purification by silica gel chromatography (1:1 ethyl acetate-hexane) gave 4-fluoro-6-methyl-benzene-1,3-diamine (613 mg, 87%).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (1:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-5b7dab3a9f2645ba933ca3fe20bfe428
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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