3-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester → HCID 19734509, compound

HRID 374164Notes

Reaction equation

HRID 374164 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].[N+]([O-])(O)=O.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([CH:28]([O:31][N+:32]([O-:34])=[O:33])[CH2:29][NH2:30])=[CH:24][CH:23]=1)([O-:21])=[O:20].C[O-].[Na+]>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:30][CH2:29][CH:28]([C:25]1[CH:26]=[CH:27][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=1)[O:31][N+:32]([O-:34])=[O:33])#[N:2]

Participants

5

Reactant 3

HCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl esterHCID 10942334Sodium MethoxideHCID 86746371HCID 86746371, compound

Product 1

HCID 19734509HCID 19734509, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-3-pyridinecarboximidate (0.22 g, 1.2 mmol) was dissolved in methanol (10 ml), and 2-(4-nitrophenyl)-2-nitroxyethylamine nitrate (0.40 g, 1.4 mmol) and sodium methoxide (0.14 g, 2.6 mmol) were added. The mixture was stirred at room temperature for 17 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residual concentrate was extracted with chlofororm (100 ml×3). The chloroform layer was washed with water (150 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with chloroform-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from methanol-diethyl ether to give the title compound (0.13 g, 0.36 mmol, yield: 31%) as colorless crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. concentrationThe residual concentrate
  3. extractionwas extracted with chlofororm (100 ml×3)
  4. washThe chloroform layer was washed with water (150 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe residual concentrate
  8. washeluting with chloroform-methanol (50:1)
  9. concentrationThe eluted fractions were concentrated under reduced pressure
  10. customcrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-cf1f6586901a4e57a1dfa9c83ee15de5
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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