4-Aminophenol → Phenolindophenol

HRID 2418638Notes

Reaction equation

HRID 2418638 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[C:10]1[CH:15]=[CH:14][C:13](N)=[C:12]([N+]([O-])=O)[C:11]=1[OH:20].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>N.O>[CH:7]1[C:2](=[N:1][C:14]2[CH:13]=[CH:12][C:11]([OH:20])=[CH:10][CH:15]=2)[CH:3]=[CH:4][C:5](=[O:8])[CH:6]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 62648Ammonium PersulfateHCID 193893123-Amino-6-methyl-2-nitrophenol

Product 1

HCID 10379Phenolindophenol

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

0.01 mole (1.09 g) of para-amino-phenol and 0.01 mole (1.68 g) of 2-methyl-5-amino-6-nitro phenol are dissolved in 15 cc of ammonia (22° Be) to which have been added 15 cc of water. To this resulting solution maintained at a temperature of about 0° C., there is added, with agitation, 0.02 mole (4.6 g) of ammonium persulfate in 20 cc of water. The agitation is maintained for 30 minutes, after which the indophenol which has precipitated in the form of its ammonium salt is filtered. The thus recovered crude product is treated with water to which has been added acetic acid to obtain the indophenol in its free form. After filtering the indophenol, washing it with water and drying it under a vacuum, there is obtained a product which melts with decomposition above 260° C.

Workup

  1. temperatureThe agitation is maintained for 30 minutes
  2. customafter which the indophenol which has precipitated in the form of its ammonium salt
  3. filtrationis filtered
  4. customThe thus recovered crude product
  5. additionis treated with water to which
  6. additionhas been added acetic acid

Sources & evidence

ORD record
ord-b1d0f763f5af43cc8caf12fec73558ab
Source dataset
uspto-grants-1984_09
Patent number
US04473374

Reaction notes

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