Ethanol, 2-amino-, 1-nitrate, nitrate (1:1) → N-cyano-N'-(2-nitroxyethyl)-3-quinolinecarboximidamide

HRID 374183

Reaction equation

HRID 374183 reaction equation
[C:1]([N:3]=[C:4]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)OC)#[N:2].[N+]([O-])(O)=O.[O:21]([CH2:25][CH2:26][NH2:27])[N+:22]([O-:24])=[O:23].C[O-].[Na+]>CO>[C:1]([NH:3][C:4]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:27][CH2:26][CH2:25][O:21][N+:22]([O-:24])=[O:23])#[N:2]

Participants

5

Reactant 3

HCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 10058988Methyl N-cyano-3-quinolinecarboximidateHCID 10942334Sodium Methoxide

Product 1

HCID 10424050N-cyano-N'-(2-nitroxyethyl)-3-quinolinecarboximidamideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl N-cyano-3-quinolinecarboximidate (0.32 g, 1.5 mmol) was dissolved in methanol (3 ml), 2-nitroxyethylamine nitrate (0.42 g, 2.5 mmol) and sodium methoxide (0.12 g, 2.2 mmol) were added. The mixture was stirred at room temperature for 18 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with dichloromethane-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from dichloromethane-diethyl ether to give the title compound (0.23 g, 0.80 mmol, yield: 54%) as colorless crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washeluting with dichloromethane-methanol (50:1)
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-97f4987ca5814880ad643d1caa6e3ad8
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Linked notes

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