Sulfuric Acid → 4-Methoxy-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1499440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499440
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=12.S(=O)(=O)(O)O.[N+:17]([O-])([O-:19])=[O:18].[K+].[OH-].[Na+]>>[CH3:1][O:2][C:3]1[C:8]([N+:17]([O-:19])=[O:18])=[CH:7][N:6]=[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=12

Komponenten

5

Edukt 4

HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 867266834-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine

Produkt 1

HCID 867266844-Methoxy-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridineAusbeute 41,4 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine (2.90 g, 19.4 mmol) was mixed with concentrated sulfuric acid (17.0 g, 173 mmol) at 0° C., then a mixture of potassium nitrate (5.3 g, 52 mmol) in another portion of concentrated sulfuric acid (26.5 g, 270 mmol) was added slowly. The reaction mixture was heated at 80° C. for 4 h. The crude mixture was slowly poured onto crushed ice (50 g), and neutralized carefully with 50% aq. NaOH to pH 8-9. The resulting mixture was extracted with EtOAc five times. The combined organic extracts were dried and concentrated under reduced pressure to give the crude sub-title compound as brown gum (1.56 g, 41%), which was used without further purification. LCMS calc. for C9H11N2O3 (M+H)+: m/z=195.1. Found: 195.2.

Aufarbeitung

  1. additionwas added slowly
  2. extractionThe resulting mixture was extracted with EtOAc five times
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f31aa18dc5640afbb9175096ca781c8
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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