Hexylamine → 2-Fluoro-n-hexyl-4-nitroaniline

HRID 56177

Reaction equation

HRID 56177 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.CCN(CC)CC.[CH2:19]([NH2:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH:25][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8102HexylamineHCID 8471TriethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 5980562-Fluoro-n-hexyl-4-nitroanilineYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-difluoronitrobenzene (3.18 g, 20 mmol) in EtOAc (50 mL) were added Et3N (2.43 g, 24 mmol) and hexan-1-amine (2.02 g, 20 mmol). The reaction mixture was refluxed overnight, then cooled to rt and concentrated in vacuo to give the title compound as yellow oil (4.37 g, 91%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ba673d1d82046bf98c0437cb95eb1a4
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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