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Sodium Hydroxide → 4-Methyl-3-(4-methylpiperazin-1-ylcarbonyl)-2-(3-nitrophenyl)-6-phenylpyridine

HRID 1722778
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1722778
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([OH:25])=O.S(Cl)(Cl)=O.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[OH-].[Na+]>C(Cl)Cl.O.CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([N:34]1[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]1)=[O:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 103595154-Methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

Produkt 1

HCID 99793004-Methyl-3-(4-methylpiperazin-1-ylcarbonyl)-2-(3-nitrophenyl)-6-phenylpyridineAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

To a mixture of 4-methyl-2-(3-nitrophenyl)-6-phenyl- 3-pyridinecarboxylic acid (1.4 g), methylene chloride (14 ml) and N,N-dimethylformamide (2.8 ml) was added a solution of thionyl chloride (0.33 ml) in methylene chloride (3 ml) at 7° C. under ice cooling. After stirring for2 hours at the same condition, a solution of 1-methylpiperazine (1.05 g) in methylene chloride (7 ml) was added thereto and the mixture was stirred for 2 hours at the same temperature. After adding Water (100 ml) and methylene chloride (50 ml) thereto, the mixture was adjusted to pH 8.5 with 10% aqueous sodium hydroxide. The organic layer was separated, washed successively with water and saturated brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethanol and diethyl ether to give 4-methyl-3-(4-methylpiperazin-1-ylcarbonyl)-2-(3-nitrophenyl)-6-phenylpyridine (0.97 g).

Aufarbeitung

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. customThe organic layer was separated
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from a mixture of ethanol and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-45b36f5ece794227b82c67f9dc4bd3c6
Quelldatensatz
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04857527

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