2-Chloro-5-nitropyridine → HCID 178526686, compound

HRID 744055Notes

Reaction equation

HRID 744055 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][NH2:9])[N:3]=[CH:2]1.Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>CC(O)C>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][NH:9][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 178510931HCID 178510931, compound

Product 1

HCID 178526686HCID 178526686, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.158 g (0.97 mmol) of 3-(1H-imidazol-4-yl)propylamine and of 0.154 g (0.97 mmol) of 2-chloro-5-nitropyridine in 10 ml of 2-propanol is brought to reflux for 21 h while stirring and evaporated under reduced pressure. The resulting residue is chromatographed on a column of silica gel, using a chloroform/methanol (1/1) mixture, to give the title compound in the form of a yellow oil. The latter is treated with oxalic acid in heated absolute ethanol to provide the oxalate salt which, after crystallization from 2-propanol, melts at 181°-182° C.

Workup

  1. temperatureto reflux for 21 h
  2. customevaporated under reduced pressure
  3. customThe resulting residue is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-cb8d021372394c4ebc7fe596ed6cb052
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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