1,3-Propanediamine → 1-(3-Aminopropylamino)-4-methoxyanthracene-9,10-dione

HRID 330059

反応式

HRID 330059 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[CH3:6][O:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:23])[C:12]=2[C:11](OC)=[CH:10][CH:9]=1>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:11]1[C:12]2[C:13](=[O:23])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:22])[C:21]=2[C:8]([O:7][CH3:6])=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 4281,3-PropanediamineHCID 2660541,4-Dimethoxyanthraquinone

生成物 1

HCID 133805771-(3-Aminopropylamino)-4-methoxyanthracene-9,10-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1,3-diaminopropane (2.07 g, 28 mmol) and 1,4 dimethoxyanthraquinone (1.50 g, 5.6 mmol) in freshly distilled CH2Cl2 (1.5 l) was fitted with a reflux condenser, and irradiated with a sunlamp for 6 h. The solvent was distilled and the crude mixture was dried in vacuo overnight. The crude product was triturated with warm petroleum ether to remove excess amine. Chromatography (silica gel CCl4 and CH2Cl2, 1:1) was performed by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone. Upon elution with methanol, a purple band slowly developed. A purple oil remained upon removal of the solvent. The oil was extracted with warm CCl4, and crystallized by adding petroleum ether to the combined CCl4 extracts. Crystallization afforded a purple solid, 0.48 g (28%) in three crops. Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample: mp 108°-110° C.; 1H NMR (CDCl3)δ9.95 (broad t, 1H), 8.21-8.25 (m, 2 H), 7.68-7.73 (m, 2 H), 7.37 (d, 1 H), 7.17 (d, 1H), 4.00(s, 3 H), 3.39-3.48 (m, 2 H), 2.94 (t,2 H), 1.86-1.98 (m, 2 H), 1.36 (broad s, 2H). Anal. Calcd. for C18H18N2O3 : C, 69.66; H, 5.85, N, 9.03. Found: C, 69.75; H 5.95; N, 8.95.

後処理

  1. customirradiated with a sunlamp for 6 h
  2. distillationThe solvent was distilled
  3. dry with materialthe crude mixture was dried in vacuo overnight
  4. customThe crude product was triturated with warm petroleum ether
  5. customto remove excess amine
  6. temperatureby slowly increasing the polarity of the solvent to CH2Cl2
  7. customto remove the unreacted 1,4-dimethoxyanthraquinone
  8. washUpon elution with methanol
  9. customA purple oil remained upon removal of the solvent
  10. extractionThe oil was extracted with warm CCl4
  11. customcrystallized
  12. additionby adding petroleum ether to the combined CCl4
  13. customCrystallization
  14. customafforded a purple solid, 0.48 g (28%) in three crops
  15. customRecrystallization
  16. additionfrom a mixture of CCl4 and petroleum ether
  17. customafforded an analytical sample

出典と根拠

ORDレコード
ord-53d5eeeede6f49438551dc0d9f136c20
出典データセット
uspto-grants-1990_01
特許番号
US04894451

関連ノート

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