Dimethylamine → 6-Chloro-N,N-dimethylnicotinamide

HRID 337283Notes

Reaction equation

HRID 337283 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH3:11][NH:12][CH3:13]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]([CH3:13])[CH3:11])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 123642316-Chloro-N,N-dimethylnicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 mL round-bottomed flask, 6-chloronicotinoyl chloride (8 g, 45.5 mmol, Eq: 1.00) was dissolved in DCM (200 ml) under argon and cooled to 0° C. To this solution, dimethylamine (90.9 ml of 2M in THF, 182 mmol, Eq: 4) was added drop-wise over 15 min maintaining the temperature below 10° C. The ice bath was removed and the reaction was stirred for 3 h.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. customThe ice bath was removed

Sources & evidence

ORD record
ord-3430a7d4f61c4caab0f557ffb543068e
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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