2,6-Dichloroaniline → 2-(2,6-Dichloroanilino)-1,3,4-trifluoroanthracene-9,10-dione

HRID 1739620Notes

Reaction equation

HRID 1739620 reaction equation
[F:1][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[C:5]([F:18])=[C:4](F)[C:3]=1[F:20].[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:23]=1[NH2:24]>>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:23]=1[NH:24][C:4]1[C:3]([F:20])=[C:2]([F: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[C:5]=1[F:18].[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:23]=1[NH:24][C:4]1[C:3]([NH:24][C:23]2[C:22]([Cl:21])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:29])=[C:2]([F: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[C:5]=1[F:18]

Participants

4

Reactant 2

HCID 118462,6-Dichloroaniline2×HCID 2833793HCID 2833793, compound

Product 2

HCID 218360252-(2,6-Dichloroanilino)-1,3,4-trifluoroanthracene-9,10-dioneHCID 218360472,3-Bis(2,6-dichloroanilino)-1,4-difluoroanthracene-9,10-dione

Procedure

2 g of 1,2,3,4-Tetrafluoroanthraquinone and 20 g of 2,6-dichloroaniline were charged in a 50 cc, four necked flask and then the reaction was carried out at 230° Cl for about 8 hours. After completion of reaction, 2,6-dichloroaniline was distilled out from the reaction solution, and a column purification thereof using a column with a silica gel was effected to give rise to 1.39 g of 2-(2,6-dichloroanilino)-1,3,4-trifluoroanthraquinone (Dye 10') (yield 46.1 mol %) and 0.78 g of 2,3-bis(2,6-dichloroanilino)-1,4-difluoroanthraquinone (Dye 25') (yield 19.4 mol %). The physical properties of Dye 10' and analytical values defining the compound are tabulated in Table 22 and the physical properties of Dye 25' and analytical values defining the compound are tabulated in Table 23.

Workup

  1. customwas carried out at 230°
  2. customfor about 8 hours
  3. distillationwas distilled out from the reaction solution
  4. customa column purification

Sources & evidence

ORD record
ord-daccf23a3d6344268d5b4bd63eaeabea
Source dataset
uspto-grants-1999_10
Patent number
US05968688

Reaction notes

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