O-Toluidine → 8-(2'-Methylanilino)-1,5-dihydroxy-4-nitro anthraquinone

HRID 1352177ノート

反応式

HRID 1352177 の反応式
[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]

参加物

4

反応物 2

HCID 7242O-ToluidineHCID 30909169,10-Anthracenedione, 1,5-dihydroxy-4,8-dinitro-

生成物 1

HCID 210999258-(2'-Methylanilino)-1,5-dihydroxy-4-nitro anthraquinone収率 33%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  1. temperatureThe solution was heated
  2. customto react at an inner temperature of 140 degrees Celsius for 4 hours
  3. temperatureThe reaction solution was cooled
  4. extractionextracted with adequate amounts of ethyl acetate and 1N-hydrochrolic acid
  5. customto separate into two layers
  6. dry with materialThe extracted organic layer was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrated solution was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-1b95233656cc4fc6b5de99bff2cbff7a
出典データセット
uspto-grants-2007_05
特許番号
US07220465B2

反応ノート

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