Triethylamine → 6-Chloro-N-methoxy-N-methylnicotinamide

HRID 1881329Notes

Reaction equation

HRID 1881329 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][O:13][CH3:14].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]([O:13][CH3:14])[CH3:11])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 114355976-Chloro-N-methoxy-N-methylnicotinamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2.3 g (12.81 mmol) of 6-chloronicotinoyl chloride and 1.53 g (15.37 mmol) of N,O-dimethylhydroxylamine in 46 mL of dichloromethane was cooled to 0° C. After dropwise addition of 5.36 mL (38.4 mmol) of triethylamine the resulting reaction mixture was warmed to RT and stirred for further 16 h. The mixture was subsequently washed with water (40 mL), 5% citric acid (40 mL), water (40 mL), and brine (40 mL). The organic layer was dried with Na2SO4, filtered, and the solvent was evaporated at reduced pressure yielding the titled compound as an oil. Amount 2.30 g. Yield 89%.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas warmed to RT
  3. washThe mixture was subsequently washed with water (40 mL), 5% citric acid (40 mL), water (40 mL), and brine (40 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-5cbd430e48d64b6498ec7699c7f78625
Source dataset
uspto-grants-2012_11
Patent number
US08318793B2

Reaction notes

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