Methyl propiolate → 1,2,3,5-Tetrahydro-1-(2-chloro-5-pyridylmethyl)-8-nitroimidazo[1,2-a]pyridin-5-one

HRID 54227

Reaktionsgleichung

Reaktionsgleichung von HRID 54227
[N+:1]([CH:4]=[C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[N:15][CH:16]=2)[CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].C[O:19][C:20](=O)[C:21]#[CH:22]>CO>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:9]2[C:5]3=[C:4]([N+:1]([O-:3])=[O:2])[CH:22]=[CH:21][C:20](=[O:19])[N:6]3[CH2:7][CH2:8]2)=[CH:16][N:15]=1

Komponenten

4

Edukt 2

HCID 13536Methyl propiolateHCID 1809572-Chloro-5-{[2-(nitromethylidene)imidazolidin-1-yl]methyl}pyridine

Produkt 1

HCID 146756711,2,3,5-Tetrahydro-1-(2-chloro-5-pyridylmethyl)-8-nitroimidazo[1,2-a]pyridin-5-oneAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixed solution of 2-nitromethylene-3-(2-chloro-5-pyridylmethyl) imidazolidine (12.7 g), propiolic acid methyl ester (4.2 g) and methanol (100 ml) was refluxed under heating for about 20 hours. Subsequently methanol was distilled off under reduced pressure, and the residue was refined by a silica-gel column chromatography to give the desired 1,2,3,5-tetrahydro-1-(2-chloro-5-pyridylmethyl)-8-nitroimidazo[1,2-a]pyridin-5-one (8 g).

Aufarbeitung

  1. temperatureunder heating for about 20 hours
  2. distillationSubsequently methanol was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d891a446f4b24759aefd04538f82426b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622956

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