HCID 69862026, compound → 2-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone

HRID 2301685Notes

Reaction equation

[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][N:10]=[CH:11][C:12]([C:19]([F:22])([F:21])[F:20])(O)[CH:13]([C:15](O)=[O:16])[CH3:14])=[C:4]([F:23])[CH:3]=1>C(O)(=O)C.N1C=CC=CC=1>[F:23][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([OH:8])=[CH:6][C:5]=1[N:9]1[C:15](=[O:16])[C:13]([CH3:14])=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=[N:10]1

Participants

Conditions

Temperature: 120 °C

Procedure

3-Carboxy-2-trifluoromethyl-2-hydroxy-1-butanal-1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone) (0.315 g) was dissolved in the mixture of acetic acid (1.0 ml) and pyridine (1.0 ml) under a nitrogen atmosphere, and stirred at 120° C. for 8 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure, and the residue was diluted with diethyl ether (100 ml). Then, the diluted solution was washed with 3N hydrochloric acid (each 20 ml) twice, and saturated sodium bicarbonate (30 ml) once, dried over magnesium sulfate, filtrated and concentrated under reduced pressure. The residue was subjected to column chromatography. Thus, 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-on (0.227 g) was obtained.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
concentrationit was concentrated under reduced pressure
additionthe residue was diluted with diethyl ether (100 ml)
washThen, the diluted solution was washed with 3N hydrochloric acid (each 20 ml) twice, and saturated sodium bicarbonate (30 ml) once
dry with materialdried over magnesium sulfate
filtrationfiltrated
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b2459dd30cbc4428a9d84b0ec963f48c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500951B1

Reaction notes

Loading…