1,2-Dichlorobenzene → 3-Chloro-1-(2-chloro-4-nitroanilino)anthracene-9,10-dione

HRID 2082861Notes

Reaction equation

HRID 2082861 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[Cl:19][C:20]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:21]=1[NH2:22].C(=O)([O-])[O-].[Na+].[Na+].ClC1C=CC=CC=1Cl>[Cu]I.O.C1(C)C=CC=CC=1.N1C=CC=CC=1>[Cl:19][C:20]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1

Participants

9

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 84922-Chloro-4-nitroanilineHCID 10340Sodium CarbonateHCID 3504831,3-Dichloroanthraquinone

Product 1

HCID 203605243-Chloro-1-(2-chloro-4-nitroanilino)anthracene-9,10-dione

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

27.7 parts of 1,3-dichloroanthraquinone, 18.15 parts of 2-chloro-4-nitroaniline and 10 parts of sodium carbonate are suspended in 400 parts of o-dichlorobenzene whilst stirring. After adding a solution of 0.4 part of copper-(I) iodide in 5 parts of pyridine and 25 parts of toluene, the mixture is kept at 160°-165° for 5 hours, whilst eliminating the water of reaction. When the mixture has cooled, it is filtered and the precipitate is washed with o-dichlorobenzene, acetone and hot water and extracted by boiling with dilute hydrochloric acid. 29 parts of 1-(2'-chloro-4'-nitroanilino)-3-chloroanthraquinone, which bulk-dyes PES in orange shades of good fastness properties, are obtained.

Workup

  1. temperatureWhen the mixture has cooled
  2. filtrationit is filtered
  3. washthe precipitate is washed with o-dichlorobenzene, acetone and hot water
  4. extractionextracted

Sources & evidence

ORD record
ord-b051fee4f18c4aa8941ee05513f01ee5
Source dataset
uspto-grants-1978_04
Patent number
US04082778

Reaction notes

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