Methylamine → (2-(Methylamino)pyridin-4-yl)methanol

HRID 1384682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384682
Cl[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][NH2:11]>C(O)C>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:11][CH3:10])[CH:7]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 7062237(2-Chloropyridin-4-yl)methanol

Produkt 1

HCID 22625034(2-(Methylamino)pyridin-4-yl)methanolAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 2-chloro-4-hydroxymethylpyridine (1.0 g, 7 mmol), (prepared as described for the starting material in Example 58), and methylamine (30 ml of a 30% solution in ethanol) was heated in a Carius tube for 16 hours at 200° C. The mixture was allowed to cool and the mixture partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer was separated, dried (MgSO4) and the volatiles removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate to give 4-hydroxymethyl-2-(methylamino)pyridine (440 mg, 46%) as a yellow oil. 1H NMR Spectrum (DMSOd6) 2.72(d, 3H); 4.35(d, 2H); 5.15(t, 1H); 6.30(br d, 1H); 6.35(d, 1H); 6.38(s, 1H); 7.85(d, 1H)

Aufarbeitung

  1. custom(prepared
  2. temperatureto cool
  3. customthe mixture partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe volatiles removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7054035e6f394f4aab176659083e82ce
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258951B1

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