2-fluoro-N-(4-methoxybutyl)-6-nitroaniline → 3-Fluoro-2-(4-methoxybutylamino)aniline

HRID 1184124Notes

Reaction equation

HRID 1184124 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH3:10]>CO.[C].[Pd]>[F:1][C:2]1[C:3]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH3:10])=[C:11]([CH:12]=[CH:13][CH:14]=1)[NH2:15]

Participants

4

Reactant 1

HCID 583552882-fluoro-N-(4-methoxybutyl)-6-nitroaniline

Product 1

HCID 583552803-Fluoro-2-(4-methoxybutylamino)anilineYield 98.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Fluoro-N-(4-methoxybutyl)-6-nitroaniline (3.54 g) was dissolved in methanol (50 ml), palladium-carbon (5%, 140 mg) was added, and the mixture was stirred for 3.5 hr under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to give the object product (3.05 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-df680b6b141e43319733a60a85e32dba
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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