HCID 15311692, compound → 3-Fluoro-4,5-dimethoxyaniline

HRID 525932Notes

Reaction equation

HRID 525932 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[O:13][CH3:14]>C(O)C.[Pt](=O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[O:13][CH3:14])[NH2:8]

Participants

4

Reactant 1

HCID 15311692HCID 15311692, compound

Product 1

HCID 574295473-Fluoro-4,5-dimethoxyanilineYield 94.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-fluoro-2,3-dimethoxy-5-nitrobenzene (91 g, 452 mmol) and platinum(IV) oxide (9 g, 39.6 mmol) in ethanol (500 mL) was hydrogenated with a Par shaker (40 psi) at r.t. for 30 min. LCMS indicated completion of the reaction. The mixture was filtered and the filtrate was concentrated to afford 3-fluoro-4,5-dimethoxyaniline (73 g, 426 mmol, 94% yield) as a brown oil that was directly used in next step. LCMS: (M+H)+:171.9.

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-98877b83722944bf9a39986f098cfcf5
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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