Dimethylformamide → 5,6-Dichloro-N-[2-(dimethylamino)ethyl]-N-methylnicotinamide

HRID 81674Notes

Reaction equation

CN(C)C=O.S(Cl)([Cl:8])=O.[Cl:10][C:11]1[C:12](O)=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16]([OH:18])=O.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][NH:25][CH3:26]>O>[Cl:10][C:11]1[C:12]([Cl:8])=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16]([N:25]([CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])[CH3:26])=[O:18]

Participants

Conditions

Temperature: 90 °C

Procedure

N,N-dimethylformamide (0.05 ml, 0.65 mmol) was added to a thionyl chloride solution (10 ml) of 5-chloro-6-hydroxynicotinic acid (1.0 g, 5.76 mmol), and stirred under a nitrogen atmosphere at 90° C. for 1 hour. The reaction solution was concentrated under reduced pressure, and with cooling with ice, N,N,N′-trimethylethane-1,2-diamine (2.32 ml, 17.3 mmol) was added to an N,N-dimethylformamide solution (10 ml) of the obtained residue, and stirred at room temperature for 3 minutes. Saturated saline water was added to the reaction solution, extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 go 1:1) to obtain 5,6-dichloro-N-[2-(dimethylamino)ethyl]-N-methylnicotinamide (1.59 g, yield: 100%) as a colorless oil.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
stirringstirred at room temperature for 3 minutes
extractionextracted with chloroform
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 go 1:1)

Sources & evidence

ORD record: ord-7f1e1229ed934e3b887e9910b557e00e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846700B2

Reaction notes

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