Dimethylamine → Methyl 6-chloro-4-(dimethylamino)nicotinate

HRID 576895

Reaktionsgleichung

Reaktionsgleichung von HRID 576895
[CH3:1][NH:2][CH3:3].Cl[C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=[C:7]([Cl:15])[CH:6]=1>CC#N>[Cl:15][C:7]1[CH:6]=[C:5]([N:2]([CH3:3])[CH3:1])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 2764083Methyl4,6-dichloronicotinate

Produkt 1

HCID 71512052Methyl 6-chloro-4-(dimethylamino)nicotinateAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dimethylamine (1.23 mL, 9.71 mmol) was slowly added to a stirred solution of methyl 4,6-dichloronicotinate (0.40 g, 1.94 mmol) in MeCN (6 mL) at room temperature. The solution was stirred at room temperature for 18 hours then concentrated in vacuo onto silica gel. Gradient chromatography, eluting with 5% EtOAc:c-Hex over 5 column volume and 5-50% over 15 column volume, gave methyl 6-chloro-4-(dimethylamino)nicotinate (335 mg, 1.56 mmol, 80% yield) as a white solid.

Aufarbeitung

  1. concentrationthen concentrated in vacuo onto silica gel
  2. washGradient chromatography, eluting with 5% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-cc1d2616d8284dbaba506880cee2d225
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040540B2

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