Pyridine → 7-Nitro-1H-indole-3-carbonitrile

HRID 1173098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173098
[CH:1]([C:3]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=O.Cl.NO.[N:18]1C=CC=CC=1.[Se](=O)=O.S([O-])([O-])(=O)=O.[Mg+2]>CN(C)C=O>[C:1]([C:3]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:18]

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 24007Selenium DioxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 443297Hydroxyamine hydrochlorideHCID 27624387-nitro-1H-indole-3-carbaldehyde

Produkt 1

HCID 223592447-Nitro-1H-indole-3-carbonitrileAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

10.15 g (53.4 mmol) of 3-formyl-7-nitro-1H-indole was dissolved in 150 ml of dimethylformamide, and 3.93 g (56.0 mmol) of hydroxylamine hydrochloride and 4.5 ml (55.6 mmol) of pyridine were added thereto. After heating under stirring at 70 to 80° C. for 2 hours, 6.3 g (56.8 mmol) of selenium dioxide and about 5 g of magnesium sulfate were added thereto. After heating at 70 to 80° C. for further 2.5 hours, the insoluble matters were filtered off and the filtrate was concentrated. Water was added thereto, and the resulting crystals were collected by filteration and successively washed with water and ethyl ether. The crystals were dissolved in a mixed solution of tetrahydrofuran and acetone, and the insoluble matters were filtered off. After concentrating the filtrate, ethyl acetate was added to the residue and the crystals were collected by filtration, to give 8.61 g of the title compound.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureAfter heating at 70 to 80° C. for further 2.5 hours
  3. filtrationthe insoluble matters were filtered off
  4. concentrationthe filtrate was concentrated
  5. additionWater was added
  6. customthe resulting crystals were collected by filteration
  7. washsuccessively washed with water and ethyl ether
  8. dissolutionThe crystals were dissolved in a mixed solution of tetrahydrofuran and acetone
  9. filtrationthe insoluble matters were filtered off
  10. concentrationAfter concentrating the filtrate, ethyl acetate
  11. additionwas added to the residue
  12. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-350a460051d34186baa5bfde951adc7f
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834049B2

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