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

HRID 393613Notes

Reaction equation

HRID 393613 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>[C:1](=[O:16])([O:14][CH3:15])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([F:12])=[CH:5][C:4]=1[CH3:13]

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), (prepared as described in EP 0307777 A2), and platinum(IV)oxide (1 74 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 (5-amino-4-fluoro-2-methylphenyl) methyl carbonate (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-7c1c26659f654994b7834cef9a7d47c1
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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