N-(3-ethoxypropyl)-2-fluoro-4-nitroaniline → HCID 28972687, compound

HRID 56181Notes

Reaction equation

HRID 56181 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[F:17])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[F:17])[CH3:2]

Participants

4

Reactant 1

HCID 28972577N-(3-ethoxypropyl)-2-fluoro-4-nitroaniline

Product 1

HCID 28972687HCID 28972687, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(3-ethoxypropyl)-2-fluoro-4-nitroaniline (8.68 g, 36 mmol) in MeOH (50 mL) was added catalyst Pd/C (0.87 g). The reaction mixture was stirred at rt under H2 overnight. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as blackish oil (5.52 g, 72%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-9e4bbe8806c34439bd6ef4ed95ef4432
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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