2-Methoxy-6-methylaniline → HCID 21836053, compound
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].[CH3:21][O:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:24]=1[NH2:25]>>[CH3:21][O:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:24]=1[NH:25][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].[CH3:21][O:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:24]=1[NH:25][C:4]1[C:3]([NH:25][C:24]2[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:23]=2[O:22][CH3:21])=[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
Procedure
2 g of 1,2,3,4-Tetrafluoroanthraquinone and 25 g of 2-methoxy-6-methylaniline were charged in a 5 cc, four necked flask and then the reaction was carried out at 80° C. for about 4 hours. After completion of reaction, 2-methoxy-6-methylaniline was distilled out from the reaction solution, and a column purification using a column with a silica gel was effected to give rise to 1.04 g of 2-(2-methoxy-6-methylanilino)-1,3,4-trifluoroanthraquinone (Dye 7') (yield 36.7 mol %) and 1.05 g of 2,3-bis(2-methoxy-6-methylanilino)-1,4-difluoroanthraquinone (Dye 20') (yield 28.6 mol %). The physical properties of Dye 7' and analytical values defining the compound are tabulated in Table 23 and the physical properties of Dye 20' and analytical values defining the compound are tabulated in Table 24.
Workup
- distillationwas distilled out from the reaction solution
- customa column purification
Sources & evidence
- ORD record
- ord-47448a32bb304a5eb6296f2b97083110
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05968688
Reaction notes
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