Sodium ethoxide → 2-ethyl-4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone

HRID 1111137Notes

Reaction equation

HRID 1111137 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([Cl:10])=[C:6]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][CH3:24])[CH:14]=2)[C:5]([N+]([O-])=O)=[N:4]1)[CH3:2].[O-:28][CH2:29][CH3:30].[Na+]>C(O)C>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([Cl:10])=[C:6]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][CH3:24])[CH:14]=2)[C:5]([O:28][CH2:29][CH3:30])=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 150790492-ethyl-4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

Product 1

HCID 150790752-ethyl-4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-ethoxy-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

300 mg of 2-ethyl-4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone (Compound No. 24) prepared in Example 4, was dissolved in 6 ml of dried ethanol, and 160 mg of sodium ethoxide was added thereto. The mixture was gently refluxed under stirring for 10 minutes. After cooling, ice water was poured into the reaction solution, and then most ethanol was distilled off under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, water and a saturated sodium chloride aqueous solution in this order and dried over sodium sulfate. The solvent was distilled off and the residual oily substance thereby obtained was purified by silica gel thin layer chromatography by using benzene:ethyl acetate (7:3 v/v) as the developer, to obtain 300 mg of the above identified compound. The physical properties and the spectrum data of NMR, IR and MS of the compound completely agreed to those of the compound prepared by the above method (1).

Workup

  1. custom24) prepared in Example 4
  2. temperatureThe mixture was gently refluxed
  3. temperatureAfter cooling
  4. distillationmost ethanol was distilled off under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washThe extract was washed with 1N hydrochloric acid, water
  7. dry with materiala saturated sodium chloride aqueous solution in this order and dried over sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residual oily substance thereby obtained
  10. customwas purified by silica gel thin layer chromatography
  11. customto obtain 300 mg of the
  12. customprepared by the above method (1)

Sources & evidence

ORD record
ord-7e0235c5351b4d539f001dd5fd295e6f
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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