2-Chloro-6-methylaniline → HCID 21836027, compound

HRID 1739624Notes

Reaction equation

HRID 1739624 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]([CH3:29])[C:23]=1[NH2:24]>>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[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]([CH3:29])[C:23]=1[NH:24][C:4]1[C:3]([NH:24][C:23]2[C:25]([CH3:29])=[CH:26][CH:27]=[CH:28][C:22]=2[Cl:21])=[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 68972-Chloro-6-methylaniline2×HCID 2833793HCID 2833793, compound

Product 2

HCID 21836027HCID 21836027, compoundHCID 21836034HCID 21836034, compound

Procedure

2 g of 1,2,3,4-Tetrafluoroanthraquinone and 25 g of 2-chloro-6-methylaniline were charged in a 50 cc, four necked flask and then the reaction was carried out at 140° C. for about 6 hours. After completion of reaction, 2-chloro-6-methylaniline was distilled out from the reaction solution and a column purification thereof was effected to give rise to 1.07 g of 2-(2-chloro-6-methylanilino)-1,3,4-trifluoroanthraquinone (Dye 8') yield 37.3 mol %) and 0.78 g of 2,3-bis(2-chloro-6-methylanilino)-1,4-difluoroanthraquinone (Dye 21') (yield 24.2 mol %). The physical properties of Dye 8' and analytical values defining the compound are tabulated in Table 22 and the physical properties of Dye 21' and analytical values defining the compound are tabulated in Table 24.

Workup

  1. distillationwas distilled out from the reaction solution
  2. customa column purification

Sources & evidence

ORD record
ord-5f957c9ab9a8433fb3c0b800ba076677
Source dataset
uspto-grants-1999_10
Patent number
US05968688

Reaction notes

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