Triethylamine → HCID 12387600, compound

HRID 2397563Notes

Reaction equation

HRID 2397563 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9](Cl)=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[Cl:12])=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[Cl:12])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

HCID 12387600HCID 12387600, compound

Procedure

55.8 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.2 mol.) are dissolved in 300 ml. of alcohol. After addition of 25 g. of triethylamine (0.25 mol.), the mixture is heated at reflux temperature and then 20 g. of N-methylpiperazine are dropped in with stirring. When the addition is completed, the temperature is maintained for 30 minutes. The solvent is distilled off, the residue is dissolved in benzene and the precipitated triethylammonium chloride filtered off. After evaporation of the solvent, the residual 4-chloro-2-methyl-6-(4-methyl-1-piperazinyl)-5-nitropyridine-3-carboxylic acid ethyl ester is recrystallized from methanol, yield 40 g. (60%), m.p. 59°-61°.

Workup

  1. additionAfter addition of 25 g
  2. temperatureat reflux temperature
  3. additionWhen the addition
  4. temperaturethe temperature is maintained for 30 minutes
  5. distillationThe solvent is distilled off
  6. dissolutionthe residue is dissolved in benzene
  7. filtrationthe precipitated triethylammonium chloride filtered off
  8. customAfter evaporation of the solvent
  9. customthe residual 4-chloro-2-methyl-6-(4-methyl-1-piperazinyl)-5-nitropyridine-3-carboxylic acid ethyl ester is recrystallized from methanol, yield 40 g

Sources & evidence

ORD record
ord-d226eb7dcf2e41739a3aa9536a64a71f
Source dataset
uspto-grants-1977_05
Patent number
US04022779

Reaction notes

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