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

HRID 1259945Notes

Reaction equation

HRID 1259945 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-36a0e02114c24adc8aa78725bb8ce313
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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