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

HRID 928774Notes

Reaction equation

HRID 928774 reaction equation
Cl.[CH3:2][O:3][NH: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:4]([O:3][CH3:2])[CH3:5])=[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

Into a 1000-mL round-bottom flask, was placed methoxy(methyl)amine hydrochloride (12 g, 123.02 mmol), triethylamine (40 g, 395.30 mmol). This was followed by the addition of a solution of 6-chloropyridine-3-carbonyl chloride (17.6 g, 100.00 mmol, Intermediate 37: step a) in dichloromethane (100 mL) dropwise with stirring. The resulting solution was stirred for 12 hours at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum to give the title compound as yellow oil.

Workup

  1. customInto a 1000-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-b29320aea1814812861606fed300a499
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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