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

HRID 255986Notes

Reaction equation

HRID 255986 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-].CCOCC.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

8

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 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 510 parts of 36% w/w hydrochloric acid containing 170 parts of anhydrous zinc chloride, are added 690 parts of o-nitroaniline. This mixture is heated to reflux temperature and, over the next hour, 708 parts of α-methylstyrene are added with stirring. On completing the addition, the reaction mixture is maintained at reflux for a further one and a half hours before being poured, whilst still hot, into a solution of 600 g sodium hydroxide in 1400 parts of water. The mixture is stirred until cool and then 1500 parts of ether are added and the resulting two phases are passed through a fibre filter to remove a small quantity of suspended solids. The filtrate is transferred to a separator and the lower aqueous phase is run off and discarded. The organic phase is washed with 2×500 parts of water, dried over magnesium sulphate, treated with decolouring charcoal and filtered. The filtrate is concentrated on a steam-bath until the residue weighed approximately 2000 parts. It is diluted with 2000 parts of 40°-60° C. petroleum-ether and set aside to crystallise overnight. The product following filtration is suspended in 1500 parts of 40°-60° petroleum-ether, stirred for 1 hour, and filtered to yield 4-cumyl-2-nitroaniline as an orange crystalline solid with a m.p. 92°-3° C. and a purity of 100% by G.L.C. analysis.

Workup

  1. temperatureThis mixture is heated
  2. temperatureto reflux temperature
  3. additionthe addition
  4. temperaturethe reaction mixture is maintained
  5. temperatureat reflux for a further one and a half hours
  6. additionbefore being poured
  7. stirringThe mixture is stirred
  8. temperatureuntil cool
  9. filtrationa fibre filter
  10. customto remove a small quantity of suspended solids
  11. washThe organic phase is washed with 2×500 parts of water
  12. dry with materialdried over magnesium sulphate
  13. additiontreated with decolouring charcoal
  14. filtrationfiltered
  15. concentrationThe filtrate is concentrated on a steam-bath until the residue
  16. additionIt is diluted with 2000 parts of 40°-60° C. petroleum-ether
  17. customto crystallise overnight
  18. filtrationfiltration
  19. customis suspended in 1500 parts of 40°-60° petroleum-ether
  20. stirringstirred for 1 hour
  21. filtrationfiltered

Sources & evidence

ORD record
ord-91610df8a08648ec828022dc1b77a9bc
Source dataset
uspto-grants-1987_10
Patent number
US04700003

Reaction notes

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