Benzene, 2-fluoro-3,4-dimethoxy-1-nitro- → 2-Fluoro-3,4-dimethoxyaniline

HRID 525886Notes

Reaction equation

HRID 525886 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-])=O>C(O)C.[Pt](=O)=O>[F:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[NH2:12]

Participants

4

Reactant 1

HCID 21999488Benzene, 2-fluoro-3,4-dimethoxy-1-nitro-

Product 1

HCID 574295482-Fluoro-3,4-dimethoxyanilineYield 95%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-3,4-dimethoxy-1-nitrobenzene (52 g, 259 mmol) was hydrogenated on a Par shaker (30 psi) in Ethanol (300 mL) with platinum(IV) oxide (5 g, 22.02 mmol) at r.t. for 30 mins. LCMS indicated completion of the reaction. The catalyst was filtered off and the filtrate was concentrated to afford 2-fluoro-3,4-dimethoxyaniline (42 g, 245 mmol, 95% yield) as a brown oil. LCMS (M+H)+: 172.0.

Workup

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

Sources & evidence

ORD record
ord-a4f963a2a2d448f2bdb0a3dba8552455
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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