Sulfuric Acid → 1,4-Dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid

HRID 1517060Notes

Reaction equation

HRID 1517060 reaction equation
[OH:1][C:2]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:8]=[C:7]([CH3:21])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:22]C1C=C(C2C=CC=C(C(F)(F)F)C=2)NC(=O)C=1C(O)=O.OS(O)(=O)=O>CO>[CH3:22][N:10]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)=[CH:8][C:7]([CH3:21])=[C:3]([C:4]([OH:6])=[O:5])[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178422656HCID 178422656, compound

Product 1

HCID 574411321,4-Dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.30 g (1.0 mmol) of 2-hydroxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid/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-a907099a0df84b65bc0e085afe9bd186
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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