HCID 10537819, compound → 4-Methoxy-5,8-dimethyl-6-nitroquinoline

HRID 1901470Notes

Reaction equation

HRID 1901470 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([CH3:16])[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=2[CH3:12])[N:5]=[CH:4][CH:3]=1.[CH3:17][O-:18].[Na+]>O.CO>[CH3:12][C:10]1[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]([CH3:16])=[C:6]2[C:11]=1[C:2]([O:18][CH3:17])=[CH:3][CH:4]=[N:5]2

Participants

5

Reactant 2

HCID 10537819HCID 10537819, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 105615364-Methoxy-5,8-dimethyl-6-nitroquinoline

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

In a flask is placed 4-chloro-5,8-dimethyl-6-nitroquinoline (1.52 g, 5.4 mmol) with sodium methoxide (2.27 g, 4.2 mmol) and methanol (25 mL). The mixture is refluxed under argon with stirring for 21 hours, diluted with water (100 mL) and methanol (50 mL) and extracted with dichloromethane (2×200 mL). The organic layer is dried over potassium carbonate, filtered and evaporated. The product is purified by flash chromatography (7/3 hexanes/ethyl acetate), yielding 5,8-dimethyl-4-methoxy-6-nitroquinoline.

Workup

  1. customIn a flask is placed
  2. temperatureThe mixture is refluxed under argon
  3. extractionextracted with dichloromethane (2×200 mL)
  4. dry with materialThe organic layer is dried over potassium carbonate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product is purified by flash chromatography (7/3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f4ed833eda9a4f6ea01fb17c627690d3
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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