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

HRID 1509451Notes

Reaction equation

HRID 1509451 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-37ea9dbf83d64683af3ae9753cc3e267
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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