Diisopropylamine → 2-Ethyl-6-methylbenzyl 5-(2-ethyl-6-methylbenzyloxy)-6-nitronicotinate

HRID 427521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427521
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18]Cl)[CH3:15].C(N[CH:29]([CH3:31])[CH3:30])(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][O:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH2:21][C:20]1[C:17]([CH3:18])=[CH:16][CH:14]=[CH:15][C:31]=1[CH2:29][CH3:30])=[O:8])[CH3:15]

Komponenten

6

Edukt 3

HCID 7912DiisopropylamineHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 183574395-Hydroxy-6-nitronicotinic acid

Produkt 1

HCID 536818842-Ethyl-6-methylbenzyl 5-(2-ethyl-6-methylbenzyloxy)-6-nitronicotinateAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-hydroxy-6-nitronicotinic acid (1 g, 5 mmol), 2-ethyl-6-methylbenzylchloride (1.85 g, 11 mmol), N,N-diisopropylamine (1.75 g, 14 mmol) and tetrabutylammonium iodide (0.1 g) was added to acetonitrile (10 ml) and was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride and washed with water. The organic layer was separated , dried and evaporated under reduced pressure. Purification of the residue by column chromatograhy on silica gel using n-hexane:methylene chloride (1:1) as eluent gave 0.7 g (29%) of the title compound.

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed with water
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customPurification of the residue by column chromatograhy on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c59e449a55fc4cd4853fe91be4e4215e
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313137B1

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