Hydrochloric Acid → 3-Isopropylaniline

HRID 461439Notes

Reaction equation

HRID 461439 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([N+:10]([O-])=O)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].Cl.[OH-].[Na+]>[Fe].C(O)C>[CH:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH2:10])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 591251HCID 591251, compound

Product 1

HCID 4586793-Isopropylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

2 G. (0.127 mole) of 3-isopropylnitrobenzene is dissolved in 300 ml. of 50% aqueous ethanol and 23 g. of iron powder is added with good stirring. The reaction mixture is brought to reflux and 13.5 ml. of a solution of 5.2 ml. of concentrated hydrochloric acid in 25 ml. of 50% aqueous ethanol is added while maintaining reflux and stirring. After 1/2 hour of stirring, the reaction mixture is made basic with 2.5 N sodium hydroxide and steam distilled. The distillate is extracted with chloroform and the chloroform layer dried and concentrated by distillation through a short vigreau column under atmospheric pressure. The residue is vacuum distilled. One fraction with boiling point of 117°-118° C. at 18 mm. Hg. contains 15.14 g. of 3-isopropylaniline which is suitable for use in the next step without further purification.

Workup

  1. temperatureto reflux
  2. temperaturewhile maintaining
  3. temperaturereflux
  4. stirringAfter 1/2 hour of stirring
  5. distillationdistilled
  6. extractionThe distillate is extracted with chloroform
  7. dry with materialthe chloroform layer dried
  8. concentrationconcentrated by distillation through a short vigreau column under atmospheric pressure
  9. distillationdistilled
  10. customof 3-isopropylaniline which is suitable for use in the next step without further purification

Sources & evidence

ORD record
ord-022cb147489846f295b840677e69de1c
Source dataset
uspto-grants-1977_12
Patent number
US04062952

Reaction notes

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