4,5-Difluoro-2-nitroaniline → 1,2-Diamino-4,5-difluorobenzene

HRID 1848137Notes

Reaction equation

HRID 1848137 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:6])=[CH:7][C:8]=1[F:9]

Participants

4

Reactant 1

HCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 27367551,2-Diamino-4,5-difluorobenzeneYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4,5-difluoro-2-nitroaniline (1.73 g, 10 mmol), palladium on activated charcoal (200 mg), and MeOH (50 mL) was stirred under hydrogen (1 atm) at rt for 12 h. The mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure to afford 4,5-difluorobenzene-1,2-diamine (1.42 g, 97%) as a brown solid, which was not purified further. 1H NMR (300 MHz, CDCl3) δ 6.50 (m, 2H), 2.75-3.48 (br s, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-19340094c8624740a271ba9a02a3552e
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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