Methanol → HCID 68671638, compound

HRID 2071171Notes

Reaction equation

HRID 2071171 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:4]=C([CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)C(N(C)C)=O.CO.C[CH2:20][O:21][C:22]([CH3:24])=[O:23].C([O-])(O)=O.[Na+]>OS(O)(=O)=O.O>[CH3:1][N:2]([CH3:16])[C:3]1[CH:4]=[C:24]([CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)[C:22]([O:21][CH3:20])=[O:23]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate2×HCID 68670658HCID 68670658, compound

Product 1

HCID 68671638HCID 68671638, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 167 mg of 2-(dimethylamino)-6-(hydroxymethyl)-N,N-dimethylisonicotinamide in 2 mL of H2SO4 and 1.2 mL of H2O was stirred at 135° C. for 12.5 h. The temperature was decreased to 95° C., methanol (5 mL) was added, and the solution was heated for 1 h. The solution was added to ice with H2O and EtOAc, and solid NaHCO3 and sat. NaHCO3 solution were added to pH=8. The aqueous layer was extracted with EtOAc (4×), and the combined extracts were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 102 mg of methyl 2-(dimethylamino)-6-(hydroxymethyl)isonicotinate as a yellow solid in 65% yield.

Workup

  1. customwas decreased to 95° C.
  2. temperaturethe solution was heated for 1 h
  3. additionwere added to pH=8
  4. extractionThe aqueous layer was extracted with EtOAc (4×)
  5. washthe combined extracts were washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash silica gel chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ca5d11da153c4c8088ac4bf0e8689f57
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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