Hydrochloric Acid → Ethyl 5-(aminomethyl)-2-(difluoromethyl)nicotinate hydrochloride
Reaktionsgleichung
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]([CH:9]([F:11])[F:10])=[N:7][CH:8]=1)#[N:2].[ClH:16].[H][H].[CH3:19]CO>[Pd]>[ClH:16].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:19])=[O:13])[C:6]([CH:9]([F:11])[F:10])=[N:7][CH:8]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Purge a mixture of methyl 5-cyano-2-(difluoromethyl)pyridine-3-carboxylate (160 g, 707.4 mmol) and EtOH (2 L) with nitrogen and stir 15 min. Add hydrochloric acid (37 wt % aqueous, 273 mL, 3183.2 mmol, 4.5 equiv) and palladium (5% on carbon, 48 g, 22.5 mmol, 0.031 equiv) in EtOH (100 mL), and stir the resulting suspension under 60 psi of hydrogen at room temperature for 70 min. Remove the solids by filtration over diatomaceous earth; wash the solid cake with EtOH (1 L); and concentrate the filtrate under reduced pressure. Repeat this procedure twice; combine the solids; and slurry in Et2O:DCM [10:1, 5.5 L]. Filter the solids and dry the resulting material at 45° C. for 3 hours to give the title compound as a light brown solid (714 g, 96% yield). MS (m/z) 216 (M+1).
Aufarbeitung
- customPurge
- customRemove the solids
- filtrationby filtration over diatomaceous earth
- washwash the solid cake with EtOH (1 L)
- concentrationand concentrate the filtrate under reduced pressure
- filtrationFilter the solids
- customdry the resulting material at 45° C. for 3 hours
Quellen und Nachweise
- ORD-Eintrag
- ord-48caa241a0a04d9cbcad565a5864bc9b
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08648200B2
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