Sodium Methoxide → Bis(3-nitrooxypropyl) 2-amino-1.4-dihydro-6-methyl-4(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 981528Notes

Reaction equation

HRID 981528 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH:7]=[C:8]([C:19]([CH3:21])=O)[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][N+:16]([O-:18])=[O:17])=[O:10])([O-:3])=[O:2].C(O)(=O)C.[C:29]([CH2:32][C:33]([O:35][CH2:36][CH2:37][CH2:38][O:39][N+:40]([O-:42])=[O:41])=[O:34])(=[NH:31])[NH2:30].C[O-].[Na+]>C(O)(C)C>[NH2:30][C:29]1[NH:31][C:19]([CH3:21])=[C:8]([C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][N+:16]([O-:18])=[O:17])=[O:10])[CH:7]([C:6]2[CH:22]=[CH:23][CH:24]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:32]=1[C:33]([O:35][CH2:36][CH2:37][CH2:38][O:39][N+:40]([O-:42])=[O:41])=[O:34]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 53888122HCID 53888122, compoundHCID 86744604HCID 86744604, compound

Product 1

HCID 10052554Bis(3-nitrooxypropyl) 2-amino-1.4-dihydro-6-methyl-4(3-nitrophenyl)pyridine-3,5-dicarboxylateYield 65.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

500 ml of an isopropanol solution containing 18.8 g (55.7 mmoles) of 3-nitrooxypropyl 2-(3-nitrobenzylidene)acetoacetate, 14.76 g (55.7 mmoles) of 3-nitrooxypropyl amidinoacetate acetate and 3.00 g (55.7 mmoles) of sodium methoxide were heated under reflux for 90 minutes. The solution was then cooled and insolubles were filtered off. The isopropanol was then evaporated off under reduced pressure. The resulting residue was dissolved in methylene chloride, and the solution was washed with water and dried over anhydrous sodium sulfate. The methylene chloride was evaporated off under reduced pressure, to give a residue, which was purified by silica gel column chromatography, eluted with a 3:1 by volume mixture of toluene and ethyl acetate, and the product was recrystallized from toluene, to afford 19.3 g (yield 65.9%) of the title compound as yellow powdery crystals, melting at 145°-146° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureThe solution was then cooled
  4. filtrationinsolubles were filtered off
  5. customThe isopropanol was then evaporated off under reduced pressure
  6. dissolutionThe resulting residue was dissolved in methylene chloride
  7. washthe solution was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe methylene chloride was evaporated off under reduced pressure
  10. customto give a residue, which
  11. customwas purified by silica gel column chromatography
  12. washeluted with a 3:1 by volume mixture of toluene and ethyl acetate
  13. customthe product was recrystallized from toluene

Sources & evidence

ORD record
ord-a44ab11729e34924824e0f8df6f315bb
Source dataset
uspto-grants-1991_02
Patent number
US04992451

Reaction notes

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