N-methyl-2-pyrrolidone → Anthrarufin

반응식

[N+]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=CC=CC=3)[C:7](=[O:19])[C:6]=2[C:5]=1[N+]([O-])=O)([O-])=O.C([O-])=[O:24].[Na+].CN1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33]>>[OH:33][C:29]1[C:13]2[C:14](=[O:18])[C:15]3[C:6](=[C:5]([OH:24])[CH:4]=[CH:17][CH:16]=3)[C:7](=[O:19])[C:8]=2[CH:32]=[CH:31][CH:30]=1.[OH:33][C:29]1[C:8]2[C:7](=[O:19])[C:6]3[C:15](=[CH:16][CH:17]=[CH:4][C:5]=3[OH:24])[C:14](=[O:18])[C:13]=2[CH:32]=[CH:31][CH:30]=1

참가 물질

반응물 3

HCID 13387N-methyl-2-pyrrolidone

HCID 425969,10-Anthracenedione, 1,2-dinitro-

HCID 2723810Sodium Formate

생성물 2

HCID 29501,8-Dihydroxyanthraquinone수율 7.5%

HCID 8328Anthrarufin수율 92.5%

실험 절차

Dinitroanthraquinone (same composition as in Example 2, 18.0 g; 0.06 mole), N-methylpyrrolidone (100 ml) and sodium formate (12.2 g; 0.18 mole) were stirred at 110° C. for 16 hours while air was sparged into the reaction mass. Product work-up as in Example 1 gave a cake of 1.9 g (92.5% 1,5-dihydroxyanthraquinone, 7.5% 1,8-dihydroxyanthraquinone) and a filtrate product of 12.0 g (4.0% 1-hydroxyanthraquinone, 88% 1,5- and 1,8-dihydroxyanthraquinone, 2.7% intermediate and 5.3% dinitroanthraquinones).