Sulfuric Acid → 2-Ethylpyrazolo[1,5-a]pyridine

HRID 408800

Reaktionsgleichung

Reaktionsgleichung von HRID 408800
[CH2:1]([C:3]1[C:11](C(O)=O)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].S(=O)(=O)(O)O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[CH2:1]([C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 583793202-Ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid

Produkt 1

HCID 161162612-Ethylpyrazolo[1,5-a]pyridineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2-Ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (4.1 g, 22 mmol) was stirred in water (100 mL) and sulfuric acid (2.5 mL) was added. The mixture was heated at 70° C. for 2 h and cooled to 20° C. The mixture was poured into ethyl acetate and neutralized with saturated sodium bicarbonate. The extracts were separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were dried (sodium sulfate) and evaporated to give the desired compound (2.6 g, 82%). LCMS for C9H11N2 (M+H)+: m/z=147.1. 1H NMR (300 MHz, DMSO-d6): δ 8.52 (m, 1H), 7.57 (m, 1H), 7.11 (m, 1H), 6.75 (m, 1H), 6.38 (s, 1H), 2.73 (m, 2H), 1.22 (m, 3H).

Aufarbeitung

  1. temperaturecooled to 20° C
  2. customThe extracts were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (sodium sulfate)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dff0416bf98646839691f01d002b0f15
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759359B2

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