1-Fluoro-2-methoxy-5-methyl-3-nitrobenzene → 3-Fluoro-2-methoxy-5-methylaniline

HRID 17286

Reaction equation

HRID 17286 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[O:12][CH3:13]>[C].[Pd].CO>[F:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[NH2:9]

Participants

4

Reactant 1

HCID 575758761-Fluoro-2-methoxy-5-methyl-3-nitrobenzene

Product 1

HCID 451220523-Fluoro-2-methoxy-5-methylanilineYield 81.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5% Palladium-carbon (wet, 100 mg) was added to a methanol (5 ml) solution of 1-fluoro-2-methoxy-5-methyl-3-nitrobenzene (I-25) (250 mg, 1.35 mmol), followed by stirring under hydrogen atmosphere for 30 minutes. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (9:1) was concentrated under reduced pressure to obtain the entitled compound (170 mg, 81%) as a yellow oily substance.

Workup

  1. filtrationAfter filtration and concentration under reduced pressure
  2. concentrationthe eluate with n-hexane:ethyl acetate (9:1) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-51c75521558b47e6890a4a69c8e9f48b
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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