Isopropyl N-cyano-4-pyridinecarboximidate → HCID 19754252, compound

HRID 374180Notes

Reaction equation

HRID 374180 reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=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]=[CH:11][N: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 10012715Isopropyl N-cyano-4-pyridinecarboximidateHCID 10942334Sodium MethoxideHCID 86746371HCID 86746371, compound

Product 1

HCID 19754252HCID 19754252, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-4-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 16 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue was extracted with chloroform (50 ml×3). The chloroform layer was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate thus obtained 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, 0.4 mmol, yield: 31%) as colorless crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionthe residue was extracted with chloroform (50 ml×3)
  3. washThe chloroform layer was washed with water (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationThe residual concentrate thus
  7. customobtained
  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-5779f16444294771b68406457b0db1a6
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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