Sodium Methoxide → HCID 178434564, compound

HRID 1762432Notes

Reaction equation

HRID 1762432 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1[N:13]1[C:17]([CH3:18])=[C:16]([N+:19]([O-:21])=[O:20])[CH:15]=[N:14]1)([O-])=O.C[O-].[Na+]>CO>[CH3:18][C:17]1[C:16]([N+:19]([O-:21])=[O:20])=[CH:15][NH:14][N:13]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 200408982-(2,4-Dinitrophenyl)-3-methyl-4-nitropyrazole

Product 1

HCID 178434564HCID 178434564, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(2,4-Dinitrophenyl)-3-methyl-4-nitropyrazole (16.0 g, 0.055 mole) was dissolved in methanol (250 ml). Sodium methoxide (11.0 g, 0.22 mole) was added dropwise as a suspension in methanol. The colour of the reaction mixture changed from yellow to a dark red. The reaction mixture was then stirred at room temperature for 3 h. The methanol was removed in vacuo to give a dark red oil, which was neutralized by pouring onto ice/HCl. The resulting brown precipitate of dinitroanisole was filtered off and discarded. The aqueous filtrate was neutralized with 10% sodium carbonate solution and extracted with ethyl acetate (3×200 ml), dried and evaporated to dryness to give a yellow solid. Crystallisation from ether/methanol gave pale yellow needles of 3-methyl-4-nitropyrazole (6.0 g, 86%).

Workup

  1. customThe methanol was removed in vacuo
  2. customto give a dark red oil, which
  3. additionby pouring onto ice/HCl
  4. filtrationThe resulting brown precipitate of dinitroanisole was filtered off
  5. extractionextracted with ethyl acetate (3×200 ml)
  6. customdried
  7. customevaporated to dryness
  8. customto give a yellow solid
  9. customCrystallisation from ether/methanol

Sources & evidence

ORD record
ord-71bc3e9ad3c5414ab4255d71d62a9458
Source dataset
uspto-grants-1989_05
Patent number
US04833136

Reaction notes

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