Water → N-Methoxy-6,N-dimethyl-nicotinamide

HRID 1186331Notes

Reaction equation

HRID 1186331 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[Cl-].C[Al+]C.[CH3:10][C:11]1[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][N:12]=1.O>ClCCl.CCCCCC>[CH3:2][N:3]([O:4][CH3:5])[C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([CH3:10])=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 231548Methyl 6-methylnicotinateHCID 16686359Dimethylalumanylium chloride

Product 1

HCID 11367353N-Methoxy-6,N-dimethyl-nicotinamideYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

N,O-dimethylhydroxylamine hydrochloride (710 mg, 7.28 mmol) was suspended in dichloromethane (50 mL). To this, dimethylaluminum chloride (a 1.04 mol/L solution in hexane, 7.00 mL, 7.28 mmol) was slowly added under a nitrogen atmosphere at 0° C. and the mixture was stirred at the same temperature for 1 hour. To this, methyl 6-methylnicotinate (1.00 g, 6.62 mmol) was added, and (7.00 mg, 1.88 mmol) was added at room temperature. Then, water was added to the reaction mixture, and extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=19/1) to give 6-methylnicotinic acid N,O-dimethylhydroxylamide (737 mg, yield: 62%).

Workup

  1. addition(7.00 mg, 1.88 mmol) was added at room temperature
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-52ca2f9dd26d46469c3a107ea4f4b9f9
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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