Ammonia → Indoaniline

HRID 653017

Reaction equation

HRID 653017 reaction equation
Cl.Cl.CO[C:5]1[CH:10]=[C:9]([NH2:11])[C:8](C)=[CH:7][C:6]=1[NH2:13].N.N[C:16]1[C:17](C)=[C:18]([OH:23])[C:19](C)=[CH:20][CH:21]=1.OO>O>[CH:16]1[C:21](=[N:13][C:6]2[CH:5]=[CH:10][C:9]([NH2:11])=[CH:8][CH:7]=2)[CH:20]=[CH:19][C:18](=[O:23])[CH:17]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 784Hydrogen PeroxideHCID 814773-Amino-2,6-dimethylphenolHCID 715871854-Methoxytoluene-2,5-diamine dihydrochloride

Product 1

HCID 24748760IndoanilineYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

0.2 mole (4.5 g) 2-methoxy-5-methyl paraphenylenediamine dihydrochloride is dissolved in 200 cc water and the pH thereof is adjusted to 8 by the addition thereto of ammonia. This solution is immediately added to 0.02 mole (2.74 g) 3-amino-2,6-dimethyl phenol, previously dissolved in 200 cc water. To the resulting mixture there are added 60 cc ammonia 22° Be and 260 cc hydrogen peroxide to make 20 volumes. The mixture is allowed to stand at room temperature for four hours. On filtering the reaction mixture on a suction filter, then are obtained 3.1 g of said indoaniline in crystalline form, which after recrystallization from a mixture of pyridine and water, exhibits a melting point of 145°.

Workup

  1. additionthe pH thereof is adjusted to 8 by the addition
  2. filtrationOn filtering the reaction mixture on a suction
  3. filtrationfilter

Sources & evidence

ORD record
ord-acbd35041ad244ada3087f779fb1536d
Source dataset
uspto-grants-1987_06
Patent number
US04675130

Linked notes

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