Methyl propiolate → 6-Hydroxy-2-methylnicotinonitrile

HRID 241687

Reaktionsgleichung

Reaktionsgleichung von HRID 241687
[NH2:1]/[C:2](/[CH3:6])=[CH:3]/[C:4]#[N:5].C[O:8][C:9](=O)[C:10]#[CH:11].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CN(C=O)C>[CH3:6][C:2]1[NH:1][C:9](=[O:8])[CH:10]=[CH:11][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 13536Methyl propiolateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 53247203-Aminocrotonitrile

Produkt 1

HCID 113785166-Hydroxy-2-methylnicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
230 °C

Versuchsvorschrift

A solution of (E)-3-amino-but-2-enenitrile (100 g) and propynoic acid methyl ester in DMF (200 ml) was stirred at 25° C. for 2 h and refluxed for additional 1 h. Dowtherm (100 ml) was added and the temperature was raised to 230° C. DMF and MeOH were distilled off. The reaction mixture was cooled down, EtOAc (200 ml) was added and the resulting crystals were filtered off and washed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.).

Aufarbeitung

  1. temperaturerefluxed for additional 1 h
  2. distillationDMF and MeOH were distilled off
  3. temperatureThe reaction mixture was cooled down
  4. additionEtOAc (200 ml) was added
  5. filtrationthe resulting crystals were filtered off
  6. washwashed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.)

Quellen und Nachweise

ORD-Eintrag
ord-61b9afaa144d4e7699a02c1b23f562a5
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653075B2

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