Formaldehyde → 5-Acetyl-2,6-dimethyl-1,4-dihydro-pyridine-3-carbonitrile

HRID 551559

Reaktionsgleichung

Reaktionsgleichung von HRID 551559
[CH3:1]/[C:2](/[NH2:6])=[CH:3]\[C:4]#[N:5].[CH3:7][C:8](=O)[CH2:9][C:10](=[O:12])[CH3:11].[CH2:14]=O>N1CCCCC1.C(O)C>[C:10]([C:9]1[CH2:14][C:3]([C:4]#[N:5])=[C:2]([CH3:1])[NH:6][C:8]=1[CH3:7])(=[O:12])[CH3:11]

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 31261AcetylacetoneHCID 53247203-Aminocrotonitrile

Produkt 1

HCID 671047185-Acetyl-2,6-dimethyl-1,4-dihydro-pyridine-3-carbonitrileAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-aminocrotonitrile (2.0 g, 24 mmol), 2,4-pentanedione (4.9 g, 49 mmol), paraformaldehyde (1.5 g, 49 mmol) and piperidine (12 drops) in ethanol (100 mL) was heated to reflux for 4 hours, cooled and concentrated to dryness. The residue was treated with diethyl ether (150 mL). The solid was collected and washed with ether. The solid was triturated with dichloromethane (2×100 mL). The combined dichloromethane triturations were concentrated to provide 2.5 g of the title compound. 1H NMR (DMSO-d6) δ ppm 1.92 (t, J=1.02 Hz, 3 H), 2.09 (s, 3 H), 2.10 (s, 3 H), 3.20 (s, 2 H), 8.65 (s, 1 H). MS (DCl-NH3) [M+H]+ at 177.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperaturecooled
  4. concentrationconcentrated to dryness
  5. additionThe residue was treated with diethyl ether (150 mL)
  6. customThe solid was collected
  7. washwashed with ether
  8. customThe solid was triturated with dichloromethane (2×100 mL)
  9. concentrationThe combined dichloromethane triturations were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6a20b9beb454439492f40b3cf539b7e2
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947711B2

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