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

HRID 1583807Notes

Reaction equation

HRID 1583807 reaction equation
[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

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 5360545SodiumHCID 120499275-Chloro-6-methoxy-4-methyl-8-nitroquinoline

Product 1

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

Procedure

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.

Workup

  1. temperatureunder reflux for 48 hr
  2. additiontreated with carbon
  3. filtrationfiltered hot
  4. washThe residue was washed with hot methanol
  5. custom15 g of 5,6-dimethoxy-4-methyl-8-nitroquinoline, separated
  6. concentrationThe filtrate was concentrated to 200 ml
  7. temperaturecooled overnight

Sources & evidence

ORD record
ord-ec156c01381045d892905f86789ebde7
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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