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

HRID 246870Notes

Reaction equation

HRID 246870 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].Cl.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:14].[OH-].[Na+]>[Cl-].[Cl-].[Zn+2].O>[CH3:12][C:13]([C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1)([CH3:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

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 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

27.6 parts of o-nitroaniline are added to a solution of 13.4 parts of anhydrous ZnCl2 in 20.4 parts of 36% hydrochloric acid. The mixture, which has been heated to the reflux temperature, has added to it dropwise, with stirring, 23.6 parts of α-methylstyrene in the course of 1 hour. After two hours of stirring at the reflux temperature the hot reaction mixture is poured into a solution of 50 parts of sodium hydroxide in 100 parts of water. After 15 minutes of stirring the mixture is allowed to cool down, whereupon the organic phase solidifies. Filtration, washing with water, drying and recrystallisation of the same from ethanol gives 4-(α,α-dimethylbenzyl)-2-nitroaniline as orange-coloured crystals having a melting point of 92°-94° C.

Workup

  1. temperatureThe mixture, which has been heated to the reflux temperature
  2. additionhas added to it dropwise
  3. customin the course of 1 hour
  4. stirringAfter two hours of stirring at the reflux temperature the hot reaction mixture
  5. stirringAfter 15 minutes of stirring the mixture
  6. temperatureto cool down, whereupon the organic phase
  7. filtrationFiltration
  8. washwashing with water
  9. customdrying
  10. customrecrystallisation of the same from ethanol

Sources & evidence

ORD record
ord-85a159689a4f42efab7b88896a630bc8
Source dataset
uspto-grants-1987_11
Patent number
US04704452

Reaction notes

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