Ethanol → (+)-1-[p-(4-Methylhexyl)anilino]-4-hydroxyanthraquinone

HRID 1075130

反応式

HRID 1075130 の反応式
Cl[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]([OH:18])=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26]([O-])(=O)[CH3:27].[Na+].C(O)C.[N+]([C:37]1[CH:42]=[CH:41]C=[CH:39][CH:38]=1)([O-])=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:39][CH:38]([CH2:26][CH3:27])[CH2:37][CH2:42][CH2:41][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7](=[O:17])[C:6]=3[C:5]([OH:18])=[CH:4][CH:3]=2)=[CH:21][CH:22]=1

参加物

7

反応物 5

HCID 702EthanolHCID 6115AnilineHCID 7416NitrobenzeneHCID 665101-Chloro-4-hydroxyanthraquinoneHCID 517045Sodium Acetate

生成物 1

HCID 20494911(+)-1-[p-(4-Methylhexyl)anilino]-4-hydroxyanthraquinone

試薬・触媒・溶媒 1

HCID 8895Cupric acetate触媒

反応条件

温度
80 °C

実験手順

1-Chloro-4-hydroxyanthraquinone (27.8 gm) is dissolved in 200 ml nitrobenzene in a boiling flask fitted with a stirrer and reflux condensor. After heating to 80° C., 18.1 gm (+)-4-methylhexyl)aniline, prepared according to Example 17, is added followed by the addition of 0.1 gm copper acetate and 20 gm sodium acetate. The mixture is stirred and heated to 150° C. for 4 hours. The mixture is then cooled to 80° C. and 500 ml ethanol is added. When cooled to room temperature the crude dye is separated by filtration, water and alcohol washed, and dried overnight. Chromatography on alumina using toluene as eluent affords the pure helichromic compound. The structure of the compound is confirmed by NMR.

後処理

  1. customfitted with a stirrer
  2. temperaturereflux condensor
  3. additionis added
  4. temperatureheated to 150° C. for 4 hours
  5. temperatureThe mixture is then cooled to 80° C.
  6. temperatureWhen cooled to room temperature the crude
  7. customdye is separated by filtration, water and alcohol
  8. washwashed
  9. customdried overnight
  10. customaffords the pure helichromic compound

出典と根拠

ORDレコード
ord-5a552999306f466fa173de75f13ffa87
出典データセット
uspto-grants-1983_07
特許番号
US04394070

関連ノート

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