Ammonia → Indoaniline

HRID 653021Notes

Reaction equation

HRID 653021 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5](NC(N)=O)=[CH:4][C:3]=1[OH:12].N.Cl.Cl.C[C:17]1[CH:22]=[C:21]([NH2:23])[C:20](OC)=[CH:19][C:18]=1[NH2:26].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O.C(O)(C)C>[CH:7]1[C:6](=[N:26][C:18]2[CH:17]=[CH:22][C:21]([NH2:23])=[CH:20][CH:19]=2)[CH:5]=[CH:4][C:3](=[O:12])[CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 62648Ammonium PersulfateHCID 85554(3-Hydroxy-p-tolyl)ureaHCID 715871854-Methoxytoluene-2,5-diamine dihydrochloride

Product 1

HCID 24748760IndoanilineYield 121.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

There is dissolved 0.5 mole (83 g) of 2-methyl-5-ureido phenol into two liters of isopropyl alcohol to which have been added six liters of ice water and two liters of ammonia (22° Be). To this solution there is added 0.5 mole (112.5 g) of 2-methyl-5-methoxy paraphenylene diamine dihydrochloride in 800 cc of water. Then little by little, and with agitation there is added 1 mole (228 g) of ammonium persulfate in 400 cc of water. The reaction mixture is then filtered to recover the above benzoquinone imine which is then washed with water, yielding 120 g of crude indoaniline. After recrystallizing the same in a mixture of dimethylformamide and water and drying the same in a vacuum at ambient temperature, the resulting product melts with decomposition at 248° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customto recover the above benzoquinone imine which
  3. washis then washed with water

Sources & evidence

ORD record
ord-bb1a31d64dc841bd8d6f6d5ca4e26df3
Source dataset
uspto-grants-1987_06
Patent number
US04675130

Reaction notes

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