Aniline → HCID 86587856, compound

HRID 393141Notes

Reaction equation

HRID 393141 reaction equation
[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:15]1[C:32]2[C:23](=[CH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[CH:31]=2)[CH:22]=[C:21]2[C:16]=1[C:17]1[CH:48]=[CH:47][C:46]3[C:33](=[CH:34][C:35]4[C:44]([CH:45]=3)=[CH:43][C:42]3[C:37](=[CH:38][C:39](Br)=[CH:40][CH:41]=3)[CH:36]=4)[C:18]=1[CH:19]=[CH:20]2>O.[Cu]>[C:1]1([NH:7][C:15]2[C:32]3[C:23](=[CH:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=4[CH:31]=3)[CH:22]=[C:21]3[C:16]=2[C:17]2[CH:48]=[CH:47][C:46]4[C:33](=[CH:34][C:35]5[C:44]([CH:45]=4)=[CH:43][C:42]4[C:37](=[CH:38][C:39]([NH:7][C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)=[CH:40][CH:41]=4)[CH:36]=5)[C:18]=2[CH:19]=[CH:20]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 86587855HCID 86587855, compound

Product 1

HCID 86587856HCID 86587856, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

Naphthacenonaphthacene is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 6,13-dibromonaphthacenonaphthacene is obtained. Phenylamine, potassium carbonate, and copper powder are added to the 6,13-dibromonaphthacenonaphthacene obtained in this way, and the mixture is reacted for 30 hours at 200° C. After the reaction solution is diluted with water, the reactant is eluted with chloroform. Thereafter, the resultant substance is purified in accordance with a usual method, and the 6,13-bis(phenylamino)naphthacenonaphthacene represented by the following formula is synthesized. (Note that, in the formula, “Ph” represents a phenyl group.)

Workup

  1. customobtained in this way
  2. customthe mixture is reacted for 30 hours at 200° C
  3. washthe reactant is eluted with chloroform
  4. customThereafter, the resultant substance is purified in accordance with a usual method
  5. customis synthesized

Sources & evidence

ORD record
ord-7f428444e4aa45698e819259a8a152e2
Source dataset
uspto-grants-2004_10
Patent number
US06805977B2

Reaction notes

Loading…