Water → N-Methoxy-N-methylisonicotinamide

HRID 627479Notes

Reaction equation

HRID 627479 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 min and 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 phase was dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography (80 g silica gel column, 100% EtOAc) to give 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 materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash column chromatography (80 g silica gel column, 100% EtOAc)

Sources & evidence

ORD record
ord-3604e5c138b54a73b1f2c76c51c9bef6
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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