Guanidine Nitrate → 4-Fluoro-2-methoxy-5-nitroaniline

HRID 1968594Notes

Reaction equation

HRID 1968594 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12].NC(N)=N.C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 10481Guanidine NitrateHCID 516892Sodium BicarbonateHCID 135322284-Fluoro-2-methoxyaniline

Product 1

HCID 574290724-Fluoro-2-methoxy-5-nitroanilineYield 83.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 4-fluoro-2-methoxyaniline (0.71 g) in concentrated sulfuric acid (7.5 mL) was added guanidine nitrate (0.61 g) under ice-cooling over 15 minutes, and the mixture was stirred at the same temperature for 15 minutes. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution cooled in ice, and the precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate, and the solution was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.78 g).

Workup

  1. temperaturecooling over 15 minutes
  2. temperaturecooled in ice
  3. filtrationthe precipitated crystals were collected by filtration
  4. dissolutionThe crystals were dissolved in ethyl acetate
  5. dry with materialthe solution was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d075466070134fe98b43032017d4d35a
Source dataset
uspto-grants-2013_04
Patent number
US08426427B2

Reaction notes

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