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

HRID 1384554Notes

Reaction equation

HRID 1384554 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.[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

4

Reactant 1

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

Product 1

HCID 226250465-Amino-4-fluoro-2-methylphenyl MethoxyformateYield 100.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of (4-fluoro-2-methyl-5-nitrophenyl) methyl carbonate (3 g, 13 mmol), (EP 0307777 A2), and platinum(IV)oxide (300 mg) in ethanol (60 ml) was stirred under hydrogen at 0.3 atmosphere for 1 hour. The catalyst was removed by filtration through diatomaceous earth and the solvent removed by evaporation to give 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (2.6 g, 100%) as a solid. 1H NMR Spectrum: (CDCl3) 2.07(s, 3H); 3.87(s, 3H); 6.52(d, 1H); 6.80(d, 1H)

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-0fcd0e2497134a93b58fe72245953181
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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