Nitrobenzene → HCID 18510034, compound

HRID 1370606Notes

Reaction equation

HRID 1370606 reaction equation
Cl[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:26]1([CH3:40])[CH:31]=[CH:30][C:29]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>[Cu].C1(C)C=CC=CC=1>[C:36]1([CH3:39])[CH:35]=[CH:34][C:33]([N:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:40])=[CH:27][CH:28]=2)[C:2]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 69293Benzenamine, 4-methyl-N-(4-methylphenyl)-HCID 18510038HCID 18510038, compound

Product 1

HCID 18510034HCID 18510034, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

In a flask were 9-α-naphthylanthracene and an equivalent amount of N-bromosuccinimide, and the reaction mixture was stirred overnight and then filtered. The filtrate was passed through a column filled with alumina. Chloroform was evaporated from the solution under a reduced pressure, and then the residue was recrystallized from petroleum ether, to give 10-chloro-9-α-naphthylanthracene. Then, in a three-necked flask were placed 10-chloro-9-α-naphthylanthracene, an equivalent amount of di-p-tolylamine, an equivalent amount of potassium carbonate, copper powder and nitrobenzene, and the mixture was stirred at 200° C. for 30 hours. After completion of the reaction, toluene was added to the mixture. The mixture was filtered to remove inorganics. Toluene and nitrobenzene were evaporated under a reduced pressure. The residue was purified by column chromatography on silica gel eluting with a 1:2 mixture of toluene and ligroin, to give 10-di-p-tolylamino-9-α-naphthylanthracene.

Workup

  1. customThen, in a three-necked flask were placed
  2. additionwas added to the mixture
  3. filtrationThe mixture was filtered
  4. customto remove inorganics
  5. customToluene and nitrobenzene were evaporated under a reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a 1:2 mixture of toluene and ligroin

Sources & evidence

ORD record
ord-ea795cba1a9a48abbe18259217bc69d6
Source dataset
uspto-grants-2003_06
Patent number
US06582837B1

Reaction notes

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