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

HRID 1625857Notes

Reaction equation

HRID 1625857 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].C(N(CC)CC)C>ClCCl>[CH3:15][O:14][N:13]([CH3:12])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 114355976-Chloro-N-methoxy-N-methylnicotinamideYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloronicotinoyl chloride (10.0 g) and N,O-dimethylhydroxyamine hydrochloride (6.65 g) in dichloromethane (200 ml) was added dropwise triethylamine (17.2 g) at 0° C. Subsequently the mixture was stirred at room temperature overnight. The mixture was washed successively with water, 5% aqueous citric acid solution, water and brine, and then, dried over sodium sulfate. The solvent was evaporated under reduced pressure to give N-methoxy-N-methyl-6-chloronicotinamide (11.73 g) as pale yellow oil. APCI-Mass m/Z 201/203 (M+H).

Workup

  1. washThe mixture was washed successively with water, 5% aqueous citric acid solution, water and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cc296f78c3b441cd89a1df5eb177dd80
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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