Acetic Acid → 2-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone

HRID 1274509

Reaktionsgleichung

Reaktionsgleichung von HRID 1274509
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][N:10]=[CH:11][C:12](=O)[C:13]([F:16])([F:15])[F:14])=[C:4]([F:18])[CH:3]=1.N1CCCCC1.[CH3:25][CH:26](C(O)=O)[C:27](O)=[O:28].C(O)(=O)C>N1C=CC=CC=1>[F:18][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([OH:8])=[CH:6][C:5]=1[N:9]1[C:27](=[O:28])[C:26]([CH3:25])=[C:12]([C:13]([F:16])([F:15])[F:14])[CH:11]=[N:10]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 487Methylmalonic AcidHCID 8082PiperidineHCID 691427153,3,3-Trifluoro-2-oxopropanal (4-chloro-2-fluoro-5-hydroxyphenylhydrazone)

Produkt 1

HCID 99490912-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinoneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Under a stream of nitrogen gas, 0.295 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone), compound 3-1 was dissolved in 2.0 ml of pyridine. To this solution were added 0.113 ml of piperidine and 0.295 g of methylmalonic acid, and the mixture was heated to 70° C. and stirred for 2.5 hours. Then, 2.0 ml of acetic acid was added, and stirring was further continued at 130° C. for 7 hours. The reaction solution was left cooling to room temperature and concentrated under reduced pressure. The residue was diluted with 100 ml of diethyl ether. The diluted solution was washed twice with 20 ml of 3 N hydrochloric acid and once with 30 ml of saturated aqueous sodium bicarbonate solution, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to column chromatography to give 0.184 g of 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one, compound 5-1.

Aufarbeitung

  1. stirringstirring
  2. waitwas further continued at 130° C. for 7 hours
  3. waitThe reaction solution was left
  4. temperaturecooling to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with 100 ml of diethyl ether
  7. washThe diluted solution was washed twice with 20 ml of 3 N hydrochloric acid and once with 30 ml of saturated aqueous sodium bicarbonate solution
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1fb5b36796cb4042baa74cf367065891
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156891

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