Ammonia → 6,7-Dihydro-3-nitro-5H-cyclopenta[b]pyridine

HRID 571977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571977
C[N:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]1=O.[C:15]1(=O)[CH2:20]CCC[CH2:16]1.N>CO>[N+:11]([C:4]1[CH:5]=[C:6]2[CH2:20][CH2:15][CH2:16][C:7]2=[N:2][CH:3]=1)([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 7967CyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Produkt 1

HCID 115645226,7-Dihydro-3-nitro-5H-cyclopenta[b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (947 mg, 4.76 mmol), cyclohexanone (0.5 mL, 5.70 mmol) and ammonia solution (1 M) in methanol (50 mL) was heated to 70° C. for 3 h under N2. TLC showed complete consumption of starting material. The reaction mixture was removed in vacuo and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford 3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (C). (340 mg, 44%)

Aufarbeitung

  1. customconsumption of starting material
  2. customThe reaction mixture was removed in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude which
  8. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c95e8641559d4568af478e97e65bf5da
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029378B2

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