Water → 5-chloro-N-methyl-2-nitroaniline

HRID 1081866Notes

Reaction equation

HRID 1081866 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([CH:15]=1)[N:7](C)[C:8](=O)C(F)(F)F.[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([CH:15]=1)[NH:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23363109HCID 23363109, compound

Product 1

HCID 2580415-chloro-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-Chloro-N-methyl-2-nitro-N-trifluoroacetylaniline (30 g) from Example 9 was dissolved in methanol (300 ml), followed by addition of an aqueous 15% NaOH solution and subsequent addition of methanol (50 ml) under stirring for 3 hours. The reaction mixture solution was poured into water (400 ml), and the precipitate was given by filtration, which was then washed with water. The precipitate was dissolved in methylene chloride (300 ml), and then the methylene chloride layer was washed with water and saturated sodium chloride solution to dry the product over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the title compound was given (19 g; 96%).

Workup

  1. filtrationthe precipitate was given by filtration, which
  2. washwas then washed with water
  3. dissolutionThe precipitate was dissolved in methylene chloride (300 ml)
  4. washthe methylene chloride layer was washed with water and saturated sodium chloride solution
  5. dry with materialto dry the product over anhydrous sodium sulfate
  6. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b22498ed62514e438d3828085055c621
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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