4-Aminophenol → Phenol, 4-amino-, 1-acetate

HRID 462653

Reaction equation

HRID 462653 reaction equation
[C:1]1(C=CC(O)=C[CH:3]=1)[OH:2].NC1C=CC=CC=1.[CH:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([OH:23])[CH:17]=1.BrC1C=CC=CC=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=1>[Cl-].[Zn+2].[Cl-]>[NH2:22][C:21]1[CH:20]=[CH:19][C:18]([OH:23])=[CH:17][C:16]=1[N+:39]([O-:41])=[O:40].[C:1]([O:38][C:35]1[CH:36]=[CH:37][C:32]([NH2:31])=[CH:33][CH:34]=1)(=[O:2])[CH3:3]

Participants

8

Reactant 5

HCID 4034-AminophenolHCID 785HydroquinoneHCID 6115AnilineHCID 7961BromobenzeneHCID 34174194-Amino-2-Nitrophenol

Product 2

HCID 83783Phenol, 4-amino-, 1-acetateHCID 37588824-Amino-3-Nitrophenol

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

4-Hydroxydiphenylamine (m.p. 70° C., b.p. 330° C.) is formed by heating hydroquinone with aniline and zinc chloride at 180°-185° C. (G. Heller, Ann., 1919, 418, p. 265; A. Calm and M. Phillip, Chem. Ber., 1883, 16, p. 1799; 1884, 17, p. 2431), or by reaction of p-aminophenol with bromobenzene and cuprous iodide (German Pat. No. 187,870). 4-Amino-2-nitrophenol (dark red plates, m.p. 128° C.) can be prepared by the procedure described in A. Girard, Bull. Soc. Chim. Fr., 1924, 35, p. 773) and 4-Amino-3-nitrophenol (m.p. 154° C.), can be formed from the nitration of 4-aminophenyl acetate as described in (Girard, loc. cit.);

Sources & evidence

ORD record
ord-5ce37c7a0e9845948ecf472ec53ff17c
Source dataset
uspto-grants-1985_05
Patent number
US04517005

Linked notes

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