2-fluoro-N,N-di-n-hexyl-4-nitroaniline → HCID 117966053, compound

HRID 56147Notes

Reaction equation

HRID 56147 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[N:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>CO.[Pd]>[F:1][C:2]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:3]=1[N:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 900241452-fluoro-N,N-di-n-hexyl-4-nitroaniline

Product 1

HCID 117966053HCID 117966053, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-N,N-di-n-hexyl-4-nitroaniline (2.79 g, 8.64 mmol) in MeOH (50 mL) was added catalyst Pd/C (0.28 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/EtOAc (V/V)=10:1) to give the title compound as pale yellow oil (1.60 g, 63%).

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)=10:1)

Sources & evidence

ORD record
ord-1e3514b894634a49afe3431ddff5b933
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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