Water → N-Methoxy-N-methylisonicotinamide

HRID 1478510Notes

Reaction equation

HRID 1478510 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.Cl.[CH3:11][NH:12][O:13][CH3:14].O>C(Cl)Cl>[CH3:14][O:13][N:12]([CH3:11])[C:7](=[O:9])[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5922Isonicotinic AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 3817473N-Methoxy-N-methylisonicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-picolinic acid (3.00 g, 24.4 mmol) and 1,1-carbonyldiimidazole (4.74 g, 29.2 mmol) in CH2Cl2 (35 mL) was stirred for ˜40 minutes, at which time it became a clear solution. After the addition of N,O-dimethylhydroxylamine hydrochloride (2.85 g, 29.2 mmol), the mixture was stirred at room temperature for 22 hours. Water was added, the organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water once, and the aqueous layer was back extracted with CH2Cl2. The organic phases were combined, dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography (80 g silica gel column, 100% EtOAc) to provide the title compound as a clear oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 22 hours
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were washed with water once
  5. extractionthe aqueous layer was back extracted with CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash column chromatography (80 g silica gel column, 100% EtOAc)

Sources & evidence

ORD record
ord-10db4ce45f884fa3b2e3b0db649df5b1
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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