Water → 4-(3-Fluoro-4-methylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxylic acid

HRID 1942162Notes

Reaction equation

HRID 1942162 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([C:16]([O:18]CC)=[O:17])=[N:12][C:11]3[CH:21]=[CH:22][CH:23]=[N:24][C:10]2=3)[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([C:16]([OH:18])=[O:17])=[N:12][C:11]3[CH:21]=[CH:22][CH:23]=[N:24][C:10]2=3)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67533114HCID 67533114, compound

Product 1

HCID 675311174-(3-Fluoro-4-methylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxylic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

45 g (0.14 mol) of ethyl 4-(3-fluoro-4-methylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxylate was dissolved in 1,4-dioxan (300 ml), and a solution of 39 g (0.28 mol) of potassium carbonate and water (300 ml) was added thereto. The solution was stirred for 1 hour at 60° C. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. Water was added to the residue thus obtained and was washed with chloroform. Then, the aqueous layer was adjusted to pH 1 by adding 6 N hydrochloric acid, and the aqueous layer was extracted again with chloroform. Anhydrous magnesium sulfate was added to the organic layer to dry the layer, and the solvent was distilled off under reduced pressure to obtain 32 g (yield: 76%) of 4-(3-fluoro-4-methylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxlic acid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionWater was added to the residue
  4. customthus obtained
  5. washwas washed with chloroform
  6. additionby adding 6 N hydrochloric acid
  7. extractionthe aqueous layer was extracted again with chloroform
  8. additionAnhydrous magnesium sulfate was added to the organic layer
  9. customto dry the layer
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fda03ea143dc4f3590a611d023acd75e
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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