Methanol → HCID 67027010, compound

HRID 1908723Notes

Reaction equation

HRID 1908723 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]=1)[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH3:28][OH:29]>OS(O)(=O)=O.O.CC(=O)OCC>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:8]=[C:9]([CH2:28][OH:29])[CH:10]=1)[CH3:2]

Participants

7

Reactant 3

HCID 887MethanolHCID 62648Ammonium Persulfate2×HCID 67026957HCID 67026957, compound

Product 1

HCID 67027010HCID 67027010, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-isobutyl-isonicotinic acid ethyl ester (1.00 g, 4.83 mmol) in methanol (50 mL) and H2SO4 (0.3 mL) is heated to 80° C. before a solution of ammonium peroxydisulfate (2.20 g, 9.65 mmol) in water (1.5 mL) is added carefully. Stirring is continued for 1 h at 80° C. before another portion of ammonium peroxydisulfate (2.20 g, 9.65 mmol) in water (1.5 mL) is added. The mixture is refluxed over night, cooled to rt, diluted with EA and washed with sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with DCM containing 10% of methanol to give 2-hydroxymethyl-6-isobutyl-isonicotinic acid ethyl ester (560 mg) as an oil; LC-MS: tR=0.81 min, [M+1]+=238.40.

Workup

  1. additionis added carefully
  2. additionis added
  3. temperatureThe mixture is refluxed over night
  4. washwashed with sat. aq. NaHCO3 solution
  5. extractionextract
  6. dry with materialis dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by CC on silica gel eluting with DCM containing 10% of methanol

Sources & evidence

ORD record
ord-55379ac658cc454299c19da1a6dc7ba7
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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