反应详情

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.

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