Sodium hydride → HCID 178496563, Verbindung

HRID 1005415

Reaktionsgleichung

Reaktionsgleichung von HRID 1005415
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:14][O:15][CH:16]1[CH2:21][CH2:20][CH:19]([CH2:22]Br)[CH2:18][CH2:17]1>CN(C=O)C.O>[N+:9]([C:3]1[C:4](=[O:8])[N:5]([CH2:22][C@H:19]2[CH2:20][CH2:21][C@@H:16]([O:15][CH3:14])[CH2:17][CH2:18]2)[CH:6]=[CH:7][C:2]=1[CH3:1])([O-:11])=[O:10]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 3453702-Hydroxy-4-methyl-3-nitropyridineHCID 217065291-(Bromomethyl)-4-methoxycyclohexane

Produkt 1

HCID 178496563HCID 178496563, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 4-methyl-3-nitro-2-pyridone (0.93 g, 6.0 mmol) and sodium hydride (60% in oil, 0.25 g, 6.3 mmol) in DMF (20 mL) was stirred at rt for 1 hour. 4-Methoxycyclohexylmethylbromide (1.5 g, 7.2 mmol) in DMF (5 mL) was added. After 60 hours, the mixture was diluted with water, and extracted with ethyl acetate. The organic phase was washed, dried (MgSO4), and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane 1/1 to 3/1) gave cis-3-nitro-1-(4-methoxycyclohexylmethyl)-4-methyl-2-pyridone which crystallized from ethyl acetate/hexane (0.16 g, 10%) and trans-3-nitro-1-(4-methoxycyclohexylmethyl)-4-methyl-2-pyridone which crystallized from ethyl acetate/hexane (0.18 g, 11%).

Aufarbeitung

  1. waitAfter 60 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-de4ff1c6810a40d098f6230f0b58e966
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06054470

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