Dimethylformamide → Methyl 2-cyano-6-methyl-4-pyridinecarboxylate

HRID 571872

Reaktionsgleichung

Reaktionsgleichung von HRID 571872
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:14]

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 2759833Methyl 2-Chloro-6-methylisonicotinate

Produkt 1

HCID 58802283Methyl 2-cyano-6-methyl-4-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Under N2, methyl 2-chloro-6-methylisonicotinate (CAS 3998-90-1) (1.000 g, 5.39 mmol, Eq: 1.00), zinc cyanide (759 mg, 6.47 mmol, Eq: 1.2) and Tetrakis-triphenylphosphin-palladium (623 mg, 539 μmol, Eq: 0.1) were mixed in DMF (17 ml). The RM was stirred under microwave at 160° C. for 30 minutes. Control with TLC: the reaction was finished. The RM was partitioned between EtOAc and water; extracted; the organic phase was dried over MgSO4; filtered; concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, 5% to 30% EtOAc in heptane). Purple solid. MS (ISP): 177.2 ([M+H]+)

Aufarbeitung

  1. customThe RM was partitioned between EtOAc and water
  2. extractionextracted
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 100 g, 5% to 30% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8aad0ea1d32840aab9b9837366dd4171
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029370B2

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