Ammonia → 3-Nitro-1-phenyl-1,2-dihydropyridin-2-one

HRID 497809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497809
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.N>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O1CCCC1.N1C=CC=CC=1>[N+:8]([C:7]1[C:2](=[O:1])[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 178526677HCID 178526677, Verbindung

Produkt 1

HCID 223191573-Nitro-1-phenyl-1,2-dihydropyridin-2-oneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5 g of 2-hydroxy-3-nitropyridine, 7.14 g of phenylboronic acid, 2.6 g of copper(II) acetate, 9.9 ml of triethylamine and 5.8 ml of pyridine were added to 100 ml of tetrahydrofuran, followed by stirring overnight. The reaction mixture was poured into aqueous ammonia, and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. The residue was suspended into ether, and collected by filtration, to give 4.71 g of the title compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-58f3150fa2c940b1840b2c8bb39e0256
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949571B2

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