4-Amino-2-chlorobenzonitrile → HCID 21836007, compound

HRID 1739627Notes

Reaction equation

HRID 1739627 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]=1F.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[C:29]#[N:30])[NH2:25]>>[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[C:29]#[N:30])[NH:25][C:4]1[C:3]([NH:25][C:24]2[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[C:22]([Cl:21])[CH:23]=2)=[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

3

Reactant 2

HCID 887284-Amino-2-chlorobenzonitrile2×HCID 2833793HCID 2833793, compound

Product 1

HCID 21836007HCID 21836007, compound

Procedure

1,2,3,4-Tetrafluoroanthraquinone and 25 g of 3-chloro-4-cyanoaniline were charged in a 50 cc, four necked flask and then the reaction was carried out at 150° C. for about 8 hours. After completion of reaction, 3-chloro-4-cyanoaniline was distilled out from the reaction solution and a column purification using a column with a silica gel was effected to give rise to 1.14 g of 2,3-bis(3-chloro-4-cyanoanilino)-1,4-difluoroanthraquinone (Dye 22') (yield 29.3 mol %). The physical properties of Dye 22' and analytical values defining the compound are tabulated in Table 23.

Workup

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

Sources & evidence

ORD record
ord-911c596038ab4722945e2253dfd8ca37
Source dataset
uspto-grants-1999_10
Patent number
US05968688

Reaction notes

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