Formaldehyde → N,2-dimethyl-4-nitrobenzenamine

HRID 918211Notes

Reaction equation

HRID 918211 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:12]=O>OS(O)(=O)=O>[CH3:12][NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 74412-Methyl-4-nitroaniline

Product 1

HCID 25282N,2-dimethyl-4-nitrobenzenamine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

15.2 g of 2-methyl-4-nitroaniline were dissolved in 150 ml conc. H2SO4 and heated in a boiling water bath. To this solution 24 g. of paraformaldehyde were added with stirring over a period of 10 minutes. The mixture was stirred an additional hour and was then cooled and poured over 300 g of ice. The precipitate was recrystallized from ethanol water to give 10.1 g of N,2-dimethyl-4-nitroaniline (m.p. 133°-136°C).

Workup

  1. temperatureheated in a boiling water bath
  2. stirringThe mixture was stirred an additional hour
  3. temperaturewas then cooled
  4. customThe precipitate was recrystallized from ethanol water

Sources & evidence

ORD record
ord-82db90b8a2ca43c4873b9c13f7bcb56f
Source dataset
uspto-grants-1976_07
Patent number
US03970423

Reaction notes

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