Sodium Methoxide → HCID 19592329, compound

HRID 613454Notes

Reaction equation

HRID 613454 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1Cl)=[CH:11][CH:10]=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])(=[O:3])[CH3:2].[CH3:18][O-:19].[Na+]>ClCCl.CO.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:19][CH3:18])=[CH:11][CH:10]=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 19592815HCID 19592815, compound

Product 1

HCID 19592329HCID 19592329, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-acetyl-4-chloro-8-nitroquinoline (339 mg) in dichloromethane was added 28% solution of sodium methoxide in methanol (0.52 mg) under ice-cooling, and the mixture was stirred for 30 minutes at ambient temperature. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane, 2:3, v/v) to give 3-acetyl-4-methoxy-8-nitroquinoline (239.3 mg).

Workup

  1. temperaturecooling
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-dc7f3c74e97a4ed6b686427c4219765a
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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