Hydrochloric Acid → Methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate

HRID 275253Notes

Reaction equation

HRID 275253 reaction equation
C(O[CH:6]=[CH:7][C:8](=O)[C:9]([F:12])([F:11])[F:10])CCC.C[CH2:15][O:16][C:17]([CH2:19][C:20]([NH2:22])=[O:21])=[O:18].C[O-].[Na+].Cl>CO.O>[O:21]=[C:20]1[C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:6][CH:7]=[C:8]([C:9]([F:10])([F:11])[F:12])[NH:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 238112Ethyl 2-carbamoylacetateHCID 2782641Butoxyvinyl trifluoromethyl ketoneHCID 10942334Sodium Methoxide

Product 1

HCID 15217844Methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylateYield 75.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 2.0 g (0.0102 mol) of 4-butoxy-1,1,1-trifluoro-3-buten-2-one (VIIIa) and 1.3 g (0.0102 mol) of ethyl malonate monoamide in 10 mL methyl alcohol was added 2.2 mL (0.0102 mol) of a 25% solution of sodium methoxide in methanol. The solution turned into a thick yellow suspension which was refluxed overnight. The suspension was cooled to room temperature, poured into water, acidified with one normal hydrochloric acid and extracted with methylene chloride. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated to afford 1.7 g (74%) of a yellow solid. m.p. 63°-64° C.; 1H NMR (CDCl3) δ4.0 (3H, s), 7.33 (1H, d, J=8 Hz), 8.4 (1H, d, J=8 Hz); IR (mineral oil) 3080, 1675 (br), 1605, 1450, 1375 cm-1.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4ee94f0d89eb4c81be9596baafedd545
Source dataset
uspto-grants-1995_02
Patent number
US05393734

Reaction notes

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