Water → 2,4-Dimethyl-5-nitroaniline

HRID 618223Notes

Reaction equation

HRID 618223 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH:12]C(=O)C.O.S(=O)(=O)(O)O>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 112848Acetamide, N-(2,4-dimethyl-5-nitrophenyl)-

Product 1

HCID 2280072,4-Dimethyl-5-nitroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2,4-dimethyl-5-nitrophenyl)acetamide, water (24 mL), concentrated sulfuric acid (12 mL), and ethanol (120 mL) was heated at reflux under an atmosphere of nitrogen for 4 hours. The ethanol was evaporated under reduced pressure and the residue partitioned between ethyl acetate (250 mL) and brine (150 mL). The brine solution was reextracted with ethyl acetate. The combined ethyl acetate extracts were then dried over magnesium sulfate. Evaporation afforded a crude product which was flash chromatographed on silica and eluted with ethyl acetate:hexane (1:4) to afford 4.63 g as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for 4 hours
  3. customThe ethanol was evaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate (250 mL) and brine (150 mL)
  5. dry with materialThe combined ethyl acetate extracts were then dried over magnesium sulfate
  6. customEvaporation

Sources & evidence

ORD record
ord-4de117abeb1f4784a6bf1ac634204bc3
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

Loading…