Isopropyl N-cyano-4-pyridinecarboximidate → HCID 19734537, compound

HRID 374181Notes

Reaction equation

HRID 374181 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.[CH3:19][CH:20]([NH2:35])[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)[O:22][N+:23]([O-:25])=[O:24].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:35][CH:20]([CH3:19])[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)[O:22][N+:23]([O-:25])=[O:24])#[N:2]

Participants

5

Reactant 3

HCID 10012715Isopropyl N-cyano-4-pyridinecarboximidateHCID 10942334Sodium MethoxideHCID 86746372HCID 86746372, compound

Product 1

HCID 19734537HCID 19734537, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl N-cyano-4-pyridinecarboximidate (0.31 g, 1.6 mmol) was dissolved in methanol (15 ml), and 1-methyl-2-(4-nitrophenyl)-2-nitroxyethylamine nitrate (0.50 g, 1.8 mmol) and sodium methoxide (0.09 g, 1.7 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 residue thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with chloroform-methanol (60:1). The eluted fractions were concentrated under reduced pressure and crystallized from diethyl ether to give the title compound (0.03 g, 0.08 mmol, yield: 5%) 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. customThe residue thus obtained
  7. washeluting with chloroform-methanol (60:1)
  8. concentrationThe eluted fractions were concentrated under reduced pressure
  9. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-1f243d2adcf7439194e65d2c1363bc35
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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