2-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene → 5-Amino-4-fluoro-2-methylphenyl Methoxyformate

HRID 1737499Notes

Reaction equation

HRID 1737499 reaction equation
[C:1](=[O:16])([O:14][CH3:15])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([F:12])=[CH:5][C:4]=1[CH3:13]>C(O)C.C(OCC)(=O)C.[Pt](=O)=O>[F:12][C:6]1[CH:5]=[C:4]([CH3:13])[C:3]([O:2][C:1]([O:14][CH3:15])=[O:16])=[CH:8][C:7]=1[NH2:9]

Participants

5

Reactant 1

HCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

Product 1

HCID 226250465-Amino-4-fluoro-2-methylphenyl MethoxyformateYield 94.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4-fluoro-2-methyl-5-nitrophenyl) methyl carbonate (8 g, 35 mmol), (EP 0307777 A2), and platinum(IV)oxide (174 mg) in ethanol (100 ml) and ethyl acetate (70 ml) was stirred under hydrogen at 1.3 atmospheres pressure for 1.5 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (7/3) to give 2-fluoro-5-methoxycarbonyloxy4-methylaniline (6.56 g, 94%) as an oil which crystallised.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed by evaporation
  3. customThe residue was purified by column chromatography
  4. washeluting with petroleum ether/ethyl acetate (7/3)

Sources & evidence

ORD record
ord-b1db3fc37c964072aac5a9f76bfa2923
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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