Benzenamine, 4-chloro-2-methoxy- → HCID 59310054, compound

HRID 1512990Notes

Reaction equation

HRID 1512990 reaction equation
[Cl: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+].[Na+]>S(=O)(=O)(O)O>[Cl: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 7143Benzenamine, 4-chloro-2-methoxy-HCID 10340Sodium CarbonateHCID 10481Guanidine Nitrate

Product 1

HCID 59310054HCID 59310054, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 4-chloro-2-methoxyaniline (1.88 g) in concentrated sulfuric acid (18 mL) was added guanidine nitrate (1.46 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 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 (1.94 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-d7e4eb6ebd8a4b7ea8de81c5d6993397
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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