Methanol → 4-Methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester

HRID 1692392Notes

Reaction equation

HRID 1692392 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[NH:5][C:4](=[O:18])[C:3]=1[C:19]([OH:21])=[O:20].OS(O)(=O)=O.[CH3:27]O>>[CH3:27][O:20][C:19]([C:3]1[C:4](=[O:18])[NH:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)=[CH:7][C:2]=1[CH3:1])=[O:21]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 57441129HCID 57441129, compound

Product 1

HCID 574411304-Methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl esterYield 77%

Procedure

A solution of 0.30 g (1.0 mmol) of 4-methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid in 15 ml of MeOH was treated with 0.06 ml=0.01 g (0.1 mmol) of H2SO4 (98%) and the reaction mixture was heated up to reflux. After 4 hours, it was cooled down to RT, poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.24 g (77%) of the title compound as off-white solid. MS: 312.0 (MH+).

Workup

  1. temperaturethe reaction mixture was heated up
  2. temperatureto reflux
  3. additionpoured
  4. extractionextracted twice with CH2Cl2
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1)

Sources & evidence

ORD record
ord-ac417e9fe225477cbd4d88f443b16253
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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