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

HRID 567358Notes

Reaction equation

HRID 567358 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-methoxyanilineYield 72%

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. This residue was chromatographed on silica gel using hexane/chloroform mixtures to afford 2.77 g (72%) of the subtitle compound. mp. 253-254° C. NMR (300 MHz, CDCl3): δ 6.88 (dd, J=10.6, 8.9, 1H); 6.32 (dd, J=7.4, 3.0, 1H); 6.20 (dt, J=8.9, 3.2,1H); 3.73 (s, 3H); 3.72 (br, 2H).

Workup

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

Sources & evidence

ORD record
ord-4dfcf519b9b8400490432340c881a514
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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