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

HRID 2168936Notes

Reaction equation

HRID 2168936 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-149db6efce8c40769801e9ebd78744aa
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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