Ammonium Hydroxide → 5-Chloro-6-methoxy-4-methyl-8-nitroquinoline

HRID 1388561Notes

Reaction equation

HRID 1388561 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=2O)[N:5]=[CH:4][CH:3]=1.[OH-].[NH4+].P(Cl)(Cl)([Cl:22])=O>>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=2[Cl:22])[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

Product 1

HCID 120499275-Chloro-6-methoxy-4-methyl-8-nitroquinolineYield 69%

Procedure

A solution of the 5-hydroxyquinoline IV (5.25 g, 0.022 mol) in phosphorus oxychloride (75 mL) was heated at 80° for 2 hours. The reaction mixture was poured onto ice and basified with excess ammonium hydroxide. The tan solid was filtered to give 5.8 g of crude product. This material was purified via column chromatography over silica gel and elution with chloroform. The fast-moving yellow band was collected and concentrated to give 3.9 g (69%) of the title compound, mp 167°-169°. Crystallization from ethanol did not raise the melting point. The crude material can also be purified by sublimation.

Workup

  1. filtrationThe tan solid was filtered
  2. customto give 5.8 g of crude product
  3. customThis material was purified via column chromatography over silica gel and elution with chloroform
  4. customThe fast-moving yellow band was collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56064a4a19c6421295fa30f49c4c9b62
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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