4-Methylmorpholine → N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide

HRID 2265987

Reaction equation

HRID 2265987 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:16][NH:17][O:18][CH3:19].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:19][O:18][N:17]([CH3:16])[C:4]([C:3]1[C:2]([CH3:1])=[N:10][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27756832-Methyl-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 86625530N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-6-trifluoromethylnicotinic acid (500 mg, 2.44 mmol) and N,O-dimethylhydroxylamine hydrochloride (285 mg, 2.92 mmol) in dichloromethane (10 mL) were added N-methylmorpholine (0.32 mL, 2.92 mmol) and N-(3-dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride (EDC, 560 mg, 2.92 mmol). The mixture was stirred at room temperature for 2 hours and washed with 1 N HCl and water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide quantitatively as oil. The crude product was used directly in the following reaction.

Workup

  1. washwashed with 1 N HCl and water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b95cf3a764647c0823983b8e57c2aa7
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Linked notes

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