Hydrochloric Acid → 2-Isopropyl-4-nitroaniline

HRID 1910756Notes

Reaction equation

HRID 1910756 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13]C(=O)C)([CH3:3])[CH3:2].Cl>C(O)C>[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH2:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45074589N-(2-Isopropyl-4-nitrophenyl)acetamide

Product 1

HCID 223794772-Isopropyl-4-nitroanilineYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(2-Isopropyl-4-nitro-phenyl)-acetamide (3 g, 13.5 mmol) was dissolved in absolute ethanol (20 mL) and 5N hydrochloric acid (20 mL) was added. The mixture was heated to reflux overnight, cooled to r.t. then concentrated in vacuo to remove the ethanol. The mixture was basified with dilute sodium hydroxide solution and extracted with ethyl acetate. The combined organic layers were washed with water and brine solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (60-120 mesh), eluting with 17% ethyl acetate/petroleum ether to afford 2-isopropyl-4-nitro-phenylamine (2.1 g, 85%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationthen concentrated in vacuo
  4. customto remove the ethanol
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with water and brine solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography on silica gel (60-120 mesh)
  10. washeluting with 17% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-835bfd5b52ea4dccb6f622c06d40901d
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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