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

HRID 623953Notes

Reaction equation

HRID 623953 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[Cl:13][C:14]1[N:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1>ClCCl>[Cl:13][C:14]1[N:19]=[CH:18][C:17]([C:20]([N:3]([O:4][CH3:5])[CH3:2])=[O:21])=[CH:16][CH:15]=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-methylnicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1000-mL round-bottom flask containing N,O-dimethylhydroxylamine hydrochloride (12.0 g, 123 mmol) and triethylamine (40.0 g, 395 mmol) was added a solution of 6-chloropyridine-3-carbonyl chloride (17.6 g, 100 mmol, Intermediate 4, step a) in dichloromethane (100 mL) dropwise. The resulting mixture was stirred for 12 hours at room temperature and filtered. The filtrate was concentrated under vacuum to give the title compound as a yellow oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-860eb4dea08140e38adb15880f5a158f
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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