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

HRID 1075130

반응식

HRID 1075130 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8895Cupric acetate촉매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a552999306f466fa173de75f13ffa87
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04394070

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