1-Chloro-5-fluoro-2-methoxy-4-nitrobenzene → 2-Fluoro-5-methoxyaniline

HRID 51445Notes

Reaction equation

HRID 51445 reaction equation
Cl[C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[O:12][CH3:13]>C(O)C.C(N(CC)CC)C.[Pd]>[F:8][C:6]1[CH:7]=[CH:2][C:3]([O:12][CH3:13])=[CH:4][C:5]=1[NH2:9]

Participants

5

Reactant 1

HCID 27792951-Chloro-5-fluoro-2-methoxy-4-nitrobenzene

Product 1

HCID 135590752-Fluoro-5-methoxyaniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5.63 g of 2-chloro-4-fluoro-5-nitroanisole in 90 ml of ethanol and 5 ml of triethylamine was hydrogenated at room temperature under 60 pounds per square inch with 1.0 g of 5% palladium on carbon for four hours. The catalyst was filtered off and the solvent was evaporated. The residue was slurried in chloroform and filtered thourough a plug of silica gel and then evaporated.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. filtrationfiltered thourough a plug of silica gel
  4. customevaporated

Sources & evidence

ORD record
ord-a23beb2c7e7741388a604740257e9a6b
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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