Methylamine → 4-Chloro-N-methylpicolinamide

HRID 78298

Reaktionsgleichung

Reaktionsgleichung von HRID 78298
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[CH3:13][NH2:14]>CO.C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:14][CH3:13])=[O:11])[CH:4]=1

Komponenten

5

Edukt 2

HCID 6329MethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Produkt 1

HCID 14768144-Chloro-N-methylpicolinamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of methyl 4-chloropyridine-2-carboxylate HCl salt (89.0 g, 428 mmol) in MeOH (75 mL) at 0° C. was treated with a 2.0 M methylamine solution in THF (1 L) at a rate which kept the internal temp. below 5° C. The resulting mixture was stored at 3° C. for 5 h, then concentrated under reduced pressure. The resulting solids were suspended in EtOAc (1 L) and filtered. The filtrate was washed with a saturated NaCl solution (500 mL), dried (Na2SO4) and concentrated under reduced pressure to afford 4-chloro-N-methyl-2-pyridinecarboxamide as pale-yellow crystals (71.2 g, 97%): mp 41-43° C.; 1H-NMR (DMSO-d6) δ 2.81 (s, 3H), 7.74 (dd, J=5.1, 2.2 Hz, 1H), 8.00 (d, J=2.2, 1H), 8.61 (d, J=5.1 Hz, 1H), 8.85 (br d, 1H); CI-MS m/z 171 ((M+H)+).

Aufarbeitung

  1. custombelow 5° C
  2. concentrationconcentrated under reduced pressure
  3. filtrationfiltered
  4. washThe filtrate was washed with a saturated NaCl solution (500 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8dcc56f8e6c04af3b8a4a71461d16393
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841330B2

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