N,N-Diethyl-2-fluoro-4-nitrobenzenamine → N1,N1-Diethyl-2-fluorobenzene-1,4-diamine

HRID 56092Notes

Reaction equation

HRID 56092 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[F:13])[CH3:2]>C1COCC1.[Pd]>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[F:13])[CH3:15]

Participants

4

Reactant 1

HCID 67995604N,N-Diethyl-2-fluoro-4-nitrobenzenamine

Product 1

HCID 33788586N1,N1-Diethyl-2-fluorobenzene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,N-diethyl-2-fluoro-4-nitroaniline (4.00 g, 18.84 mmol) in THF (50 mL) was added Pd/C (1.50 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (3.20 g, 93%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6ffd0bf7ba66423e891486dba4f1b90e
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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