Butyric Acid → 7-Methyl-2-propyl-1H-imidazo[4,5-b]pyridine

HRID 466674

Reaktionsgleichung

Reaktionsgleichung von HRID 466674
[C:1](O)(=O)[CH2:2][CH2:3][CH3:4].[NH2:7][C:8]1[C:13]([NH2:14])=[C:12]([CH3:15])[CH:11]=[CH:10][N:9]=1.[NH4+].[OH-]>>[CH3:15][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[N:7]=[C:1]([CH2:2][CH2:3][CH3:4])[NH:14][C:13]=12

Komponenten

4

Edukt 3

HCID 264Butyric AcidHCID 14923Ammonium HydroxideHCID 3174954-Methylpyridine-2,3-diamine

Produkt 1

HCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridineAusbeute 95 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of butyric acid (6.57 mL, 71.9 mmol), 2,3-diamino-4-picoline (8.05 g, 65.4 mmol) (Lappin, G. R., Slezak, F. B. J. Am. Chem. Soc. (1950) 72, 7806-7) and polyphosphoric acid (50 g) was heated to 100° C. with stirring for 3 hours. The reaction was monitored by tlc of NH4OH neutralized aliquots. Basification (NH4OH), extraction (CH2Cl2, 4×50 mL), drying (K2CO3), purification (by filtering through 100 g SiO2, EtOAc elution), and concentration gave 10.0 g (95%) of the title compound as an amorphous tan solid which was judged pure by 1H NMR and tlc: mp 110°-112° C. (without recrystallization).

Aufarbeitung

  1. extractionBasification (NH4OH), extraction (CH2Cl2, 4×50 mL)
  2. customdrying
  3. custom(K2CO3), purification (by filtering through 100 g SiO2, EtOAc elution), and concentration

Quellen und Nachweise

ORD-Eintrag
ord-f605456e6c7c4dcbadc5c02a0b2586d5
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157026

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