Citric Acid → HCID 15457048, compound

HRID 992860Notes

Reaction equation

HRID 992860 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=O)[O:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)=[C:4]([F:19])[CH:3]=1.[CH3:20][NH2:21].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:10])[N:21]([CH3:20])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6101p-Toluenesulfonic acidHCID 18408352HCID 18408352, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 15457048HCID 15457048, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.3 g (32 mmol) of 3-(4-chloro-2-fluorophenyl)-6-trifluoromethyl-2H-pyran-2-one was added to 160 ml of methanol, and 3.8 g (48 mmol) of a 40% methylamine/methanol solution was dropwise added under cooling with ice, followed by stirring for 2 hours under cooling with ice. This reaction solution was acidified by an addition of a 10% citric acid aqueous solution and then extracted with ethyl acetate, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The obtained residue was dissolved in 160 ml of toluene, and 0.4 g (2.1 mmol) of p-toluenesulfonic acid was added thereto, followed by refluxing for 4 hours. After cooling, the reaction solution was washed with water. Then, the organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography to obtain 5.7 g (19 mmol) of the desired product. Melting point: 103-104° C.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. extractionextracted with ethyl acetate
  5. washby washing with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. dissolutionThe obtained residue was dissolved in 160 ml of toluene
  9. temperatureby refluxing for 4 hours
  10. temperatureAfter cooling
  11. washthe reaction solution was washed with water
  12. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  13. distillationthe solvent was distilled off
  14. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3bbe6d7af0d5420986bd773f7a7459e0
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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