Dichloromethane → N1,N1-di-n-butyl-2-fluorobenzene-1,4-diamine

HRID 56141Notes

Reaction equation

HRID 56141 reaction equation
[CH2:1]([N:5]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[F:15])[CH2:2][CH2:3][CH3:4].C(Cl)Cl>[Pd].CO>[CH2:1]([N:5]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[F:15])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 117966115HCID 117966115, compound

Product 1

HCID 28982364N1,N1-di-n-butyl-2-fluorobenzene-1,4-diamineYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N,N-di-n-butyl-2-fluoro-4-nitroaniline (4.03 g, 15 mmol) in mixed solvents of CH2Cl2 (70 mL) and MeOH (20 mL) was added catalyst Pd/C (0.40 g). 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/CH2Cl2 (V/V)=8:1) to give the title compound as colorless oil (2.32 g, 65%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=8:1)

Sources & evidence

ORD record
ord-99c1c09f8b15485a8c3b3c565d3731eb
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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