Hydrochloric Acid → 5,6-Dimethyl-2-pyridone

HRID 603504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 603504
[CH3:1][C:2]1[CH:3]=[C:4](C#N)[C:5](=[O:9])[NH:6][C:7]=1[CH3:8].Cl.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5905325,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 1197855,6-Dimethyl-2-pyridoneAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
175 °C

Versuchsvorschrift

A 100 mL Parr reactor was charged with 5,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (Example 475, 3.00 g, 20.3 mmol), concentrated hydrochloric acid (18 mL), and water (18 mL). The reactor was slowly heated to 175° C. for 9 h and then cooled to rt. The solution was basified with 1N NaOH in water and was extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, and concentrated in vacuo, yielding the title compound (1.21 g, 48%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.36 (bs, 1H), 7.18 (d, 1H), 6.04 (d, 1H), 2.10 (s, 3H), 1.93 (s, 3H).

Aufarbeitung

  1. temperaturecooled to rt
  2. extractionwas extracted with EtOAc
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-01411a0e5cce4fcc96e5371a953cf923
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906653B2

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