Reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:20])[CH:10]=[CH:11][C:12]=3[N+:17]([O-])=O)[C:7](=[O:21])[C:6]=2[C:5]([N+:22]([O-:24])=[O:23])=[CH:4][CH:3]=1.[CH3:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1N>CC(N(C)C)=O>[CH3:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH:17][C:12]1[CH:11]=[CH:10][C:9]([OH:20])=[C:8]2[C:13]=1[C:14](=[O:16])[C:15]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]([N+:22]([O-:24])=[O:23])[C:6]=1[C:7]2=[O:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 25 g of 1,5-dihydroxy-4,8-dinitroanthraquinone and a 25 g of 2-methylaniline were dissolved in 250 ml of dimethylacetamide. The solution was heated and allowed to react at an inner temperature of 140 degrees Celsius for 4 hours. The reaction solution was cooled, and then extracted with adequate amounts of ethyl acetate and 1N-hydrochrolic acid to separate into two layers. The extracted organic layer was dried with magnesium sulfate and then concentrated. The concentrated solution was purified by silica gel chromatography to give a 9.7 g of 8-(2′-methylanilino)-1,5-dihydroxy-4-nitroanthraquinone in a 33% yield.
Workup
- temperatureThe solution was heated
- customto react at an inner temperature of 140 degrees Celsius for 4 hours
- temperatureThe reaction solution was cooled
- extractionextracted with adequate amounts of ethyl acetate and 1N-hydrochrolic acid
- customto separate into two layers
- dry with materialThe extracted organic layer was dried with magnesium sulfate
- concentrationconcentrated
- customThe concentrated solution was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-1b95233656cc4fc6b5de99bff2cbff7a
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07220465B2
Linked notes
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