Nitrobenzene → 1-(2-Chloro-4-nitroanilino)-5-methoxyanthracene-9,10-dione

HRID 2082862Notes

Reaction equation

HRID 2082862 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH3:18])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[Cl:30].C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]Cl>[Cl:30][C:22]1[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=1[NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH3:18])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 10340Sodium CarbonateHCID 346671-Bromo-2-chloro-4-nitrobenzeneHCID 138979031-Amino-5-methoxyanthracene-9,10-dione

Product 1

HCID 203605261-(2-Chloro-4-nitroanilino)-5-methoxyanthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

12.65 parts of 1-amino-5-methoxyanthraquinone, 15.3 parts of 1-bromo-2-chloro-4-nitrobenzene, 5 parts of sodium carbonate and 1 part of copper-(I) chloride in 120 parts of nitrobenzene are stirred for 3 hours at 170°. To remove the water formed during the reaction, a stream of nitrogen is passed through the apparatus during the reaction. After cooling the reaction mixture to 25°, the 1-(2'-chloro-4'-nitroanilino)-5-methoxyanthraquinone formed is filtered off, washed with nitrobenzene, ethanol and hot water and extracted by boiling with 5% strength hydrochloric acid. The colorant is obtained in a yield of 19.5 parts, that is to say 95% of theory. It bulk-dyes polyester in an orange-coloured shade having excellent fastness properties.

Workup

  1. customTo remove the water
  2. customformed during the reaction
  3. customa stream of nitrogen is passed through the apparatus during the reaction
  4. temperatureAfter cooling the reaction mixture to 25°

Sources & evidence

ORD record
ord-2c689383312e40a5a1fd3218eee2f46d
Source dataset
uspto-grants-1978_04
Patent number
US04082778

Reaction notes

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