Dichloromethane → 2-fluoro-N1,N1-diisobutylbenzene-1,4-diamine

HRID 56144Notes

Reaction equation

HRID 56144 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[N:4]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][CH:6]([CH3:8])[CH3:7].C(Cl)Cl>[Pd].CO>[F:1][C:2]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:3]=1[N:4]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 900231022-fluoro-N,N-diisobutyl-4-nitroaniline

Product 1

HCID 435878672-fluoro-N1,N1-diisobutylbenzene-1,4-diamineYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-N,N-diisobutyl-4-nitroaniline (0.8 g, 3 mmol) in mixed solvents of CH2Cl2 (15 mL) and MeOH (15 mL) was added catalyst Pd/C (80 mg). The reaction mixture was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as pale yellow oil (0.40 g, 56%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1)

Sources & evidence

ORD record
ord-4afc4c920a5646fcb271d1c966889412
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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