Methanol → 2-Amino-4-methyl-3,5-pyridinedicarbonitrile

HRID 4447

Reaktionsgleichung

Reaktionsgleichung von HRID 4447
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]#[N:12])=[C:4](Cl)[N:3]=1.CO.C1CCCCC1.CCOC(C)=O>CN(C=O)C.[Pd]>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]#[N:12])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 6060002-Amino-6-chloro-4-methylpyridine-3,5-dicarbonitrileHCID 21867204Cyclohexane ethylacetate

Produkt 1

HCID 110300832-Amino-4-methyl-3,5-pyridinedicarbonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Hydrogenolysis of 4 (10.0 g, 52.0 mmol) in DMF (150 mL)-MeOH (75 mL) containing 5% Pd on BaCO3 (10.0 g) was carried out in a Parr shaker with H2 pressure kept near 3.5 kg/cm2 (50 psi) for six hours. The mixture was then filtered (Celite mat), and evaporated to dryness (final conditions <1 mm, bath to 45° C.) The residue containing Ba salts which separated during the evaporation was stirred with H2O (100 mL) to give the H2O-insoluble product (7.74 g). Recrystallization from EtOH (800 mL) then gave pure 6, mp 222°-223° C., in 86% yield (7.1 g); homogeneous by TLC (cyclohexane-EtOAc, 1:1); 1H NMR (Me2SO-d6) δ2.50 (s, CH3), 7.82 (s, NH2), 8.50 (s, C2 --H).

Aufarbeitung

  1. customfor six hours
  2. filtrationThe mixture was then filtered (Celite mat)
  3. customevaporated to dryness (final conditions <1 mm, bath to 45° C.) The residue
  4. additioncontaining Ba salts which
  5. customseparated during the evaporation
  6. customto give the H2O-insoluble product (7.74 g)
  7. customRecrystallization from EtOH (800 mL)
  8. customthen gave pure 6, mp 222°-223° C.

Quellen und Nachweise

ORD-Eintrag
ord-717477a32b7f4cc0977022329f06cd51
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725687

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