Methanol → 6-(Methylamino)nicotinaldehyde

HRID 534775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534775
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#N)=[CH:5][CH:4]=1.CC(C[Al]CC(C)C)C.CO.[OH:22]S(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:22])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 16682954DibahHCID 178608996-(Methylamino)pyridine-3-carbonitrile

Produkt 1

HCID 184162986-(Methylamino)nicotinaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To 6-(methylamino)-3-pyridinecarbonitrile (D94) (0.1 g, 0.752 mmol) in toluene (10 mL) cooled to −78 C under argon was added Dibal-H (1.88 mL, 1M solution in toluene, 11.2 mmol) dropwise. The reaction was stirred at −78° C. and then allowed to warm to room temperature overnight. MeOH (0.47 mL) and 2 M H2SO4 (1.42 mL) were added and mixture was stirred for 1.5 h then concentrated in vacuo. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried and concentrated to give the title compound (0.067 g). δH (CDCl3, 400 MHz) 9.78 (1H, s), 8.52 (1H, d), 7.92 (1H, dd), 6.45 (1H, d), 5.38 (1H, br.s), 3.04 (3H, d). MS (ES): MH+ 137.1.

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. stirringmixture was stirred for 1.5 h
  3. concentrationthen concentrated in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. customthe combined organic layers were dried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-055b213759f34416bed1dfd49fc46710
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853218B2

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