Methanol → 4-Methyl-5,6-dimethoxy-8-nitroquinoline

反応式

[Na].Cl[C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([N+:15]([O-:17])=[O:16])=[C:9]2[C:4]=1[C:5]([CH3:18])=[CH:6][CH:7]=[N:8]2.N1C=CC=CC=1.[CH3:25][OH:26]>>[CH3:25][O:26][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([N+:15]([O-:17])=[O:16])=[C:9]2[C:4]=1[C:5]([CH3:18])=[CH:6][CH:7]=[N:8]2

参加物

反応物 4

HCID 887Methanol

HCID 1049Pyridine

HCID 5360545Sodium

HCID 120499275-Chloro-6-methoxy-4-methyl-8-nitroquinoline

生成物 1

HCID 6191084-Methyl-5,6-dimethoxy-8-nitroquinoline

実験手順

To a solution of sodium metal (4.8 g, 0.2 g. atom) in methanol (300 ml) were added 50.6 g (0.2 mole) of 5-chloro-6-methoxy-4-methyl-8-nitroquinoline and 70 ml of pyridine. The mixture was stirred under reflux for 48 hr, treated with carbon and filtered hot. The residue was washed with hot methanol and the filtrate and washings were combined (total, 600 ml). On standing, 15 g of 5,6-dimethoxy-4-methyl-8-nitroquinoline, separated, mp 120°-124°. The filtrate was concentrated to 200 ml and cooled overnight to give an additional 15 g of 5,6-dimethoxy-4-methyl-8-nitroquinoline. Dilution of this filtrate with 6 liters of water provided 7 g of product for a total crude yield of 37 g. Crystallization from methanol (carbon) gave 34 g (68%) of 5,6-dimethoxy-4-methyl-8-nitroquinoline, mp 123°-125°. The same compound (m.p. and mixed m.p. 123°-125°) resulted when a Skraup reaction was performed on 4-amino-5-nitroveratrole and methyl vinyl ketone.