Acetic Acid → 7-Nitro-1-oxo-2-(2-pyridylmethylidene)-1,2,3,4-tetrahydronaphthalene

HRID 7059

Reaktionsgleichung

Reaktionsgleichung von HRID 7059
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]=O.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[CH:21][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)[C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 142732-PyridinecarboxaldehydeHCID 384457-Nitro-1-tetralone

Produkt 1

HCID 696642877-Nitro-1-oxo-2-(2-pyridylmethylidene)-1,2,3,4-tetrahydronaphthaleneAusbeute 19,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

7-Nitro-1-tetralone (500 mg), pyridine-2-aldehyde (315 mg), piperidine (0.15 ml) and acetic acid (0.4 ml) are dissolved in toluene (10 ml), and the mixture is heated under reflux for 12 hours. The reaction solution is washed with water, and the organic layer is dried over sodium sulfate. The solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 7-nitro-1-oxo-2-(2-pyridylmethylidene)-1,2,3,4-tetrahydronaphthalene (140 mg).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. washThe reaction solution is washed with water
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. customThe solvent is evaporated under reduced pressure
  6. customThe residue is purified by silica gel chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8189913a89c34604a80c6e562e94b274
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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