Hydrochloric Acid → 2-Nitro-4-(2-phenylpropan-2-yl)aniline

HRID 255984Notes

Reaction equation

HRID 255984 reaction equation
Cl.[N+:2]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([O-:4])=[O:3].[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:14].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].O>[C:13]([C:10]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:2]([O-:4])=[O:3])[CH:11]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 7407Alpha-MethylstyreneHCID 14798Sodium Hydroxide

Product 1

HCID 139078392-Nitro-4-(2-phenylpropan-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3007855ZincchlorideSolvent

Procedure

To 20.4 parts of 36% w/w hydrochloric acid in which had previously been dissolved 13.4 parts of anhydrous zinc chloride is added 27.6 parts of o-nitroaniline. This mixture is heated to reflux temperature and during the next hour 23.6 parts of α-methylstyrene are added dropwise with stirring. After completing the addition the reaction mixture is stirred and refluxed for further 2 hours before being poured whilst still hot into a solution of 50 parts sodium hydroxide in 100 parts of water. This mixture after stirring for 15 minutes is set aside to cool, whereupon the upper organic phase solidified. The solid cake is then broken up, filtered off, washed with water, dried, and crystallised from ethanol to give 4-cumyl-2-nitro-aniline as orange crystals m.p. 92°-4° C. with the following percentage composition by weight.

Workup

  1. temperatureThis mixture is heated
  2. temperatureto reflux temperature
  3. additionthe addition the reaction mixture
  4. stirringis stirred
  5. temperaturerefluxed for further 2 hours
  6. stirringThis mixture after stirring for 15 minutes
  7. temperatureto cool, whereupon the upper organic phase
  8. filtrationfiltered off
  9. washwashed with water
  10. customdried
  11. customcrystallised from ethanol

Sources & evidence

ORD record
ord-9d3fce17b1344b07be5074c4e3271bea
Source dataset
uspto-grants-1987_10
Patent number
US04700003

Reaction notes

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