2-Aminophenol → 3'-Chloro-2'-hydroxy-p-toluanilide

HRID 268488Notes

Reaction equation

HRID 268488 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].[NH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=1[OH:19].N[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27].[C:28]1(C)C=CC(Cl)=CC=1>>[Cl:8][C:4]1[C:3]([OH:9])=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:1][C:22]([C:12]1[CH:13]=[CH:14][C:15]([CH3:28])=[CH:16][CH:11]=1)=[O:27].[Cl:18][C:13]1[C:12]([OH:19])=[C:11]([CH:16]=[C:15]([Cl:17])[CH:14]=1)[NH:10][C:3]([C:21]1[CH:26]=[CH:25][C:24]([CH3:28])=[CH:23][CH:22]=1)=[O:9]

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 78104-ChlorotolueneHCID 106992-Amino-4,6-dichlorophenolHCID 64860252-Amino-6-chlorophenol

Product 2

HCID 214138063'-Chloro-2'-hydroxy-p-toluanilideHCID 214138573',5'-Dichloro-2'-hydroxy-p-toluanilide

Procedure

When 2-amino-6-chlorophenol and 2-amino-4,6-dichlorophenol are used in place of o-aminophenol and when p-toluyl chloride is used in place of 3-fluoro-p-toluyl chloride in the above example, there is obtained 3'-chloro-2'-hydroxy-p-toluanilide and 3',5'-dichloro-2'-hydroxy-p-toluanilide, respectively.

Sources & evidence

ORD record
ord-ebb6f6b60bdc4f6fb78847ba22460020
Source dataset
uspto-grants-1976_03
Patent number
US03947582

Reaction notes

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