1079-73-8|6-(4-Chlorophenyl)-4,5-dihydropyridazin-3(2H)-one| Ambeed

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CAS No. :	1079-73-8
Formula :	C₁₀H₉ClN₂O
M.W :	208.64
SMILES Code :	O=C1CCC(C2=CC=C(Cl)C=C2)=NN1
MDL No. :	MFCD00276381

Yield	Reaction Conditions	Operation in experiment
10.83 g (89%)	With bromine; In water; acetic acid;	a. 6-(4-chlorophenyl)pyridazinone To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60-70 C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone.
		General procedure: solution of 0.043 mol bromine in 25 ml glacial acetic acid wasadded drop wise to a solution of 0.039 mol 6-(2-fluoro-4-methoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone in 100 ml glacialacetic acid at 60-70 C, then the reaction mixture was refluxedfor 3 h. After cooling to 5 C, it was poured into ice water and converted to the free base form with ammonium hydroxide. Theprecipitate was collected byfiltration, washed with water untilneutral, dried, and crystallized from ethanol-water [38].

Yield	Reaction Conditions	Operation in experiment
	In water; acetic acid; ethyl acetate;	EXAMPLE 12 Preparation of 6-(p-chlorophenyl)-3-methyl-1,2,4-triazolo[4,3-b]pyridazine A 47.5 g. portion of 6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone (prepared as in Example 1 of U.S. Pat. No. 3,689,652) is dissolved in 250 ml. of glacial acetic acid at 65-70 C. with stirring. Then a solution of 14 ml. (42 g.) of bromine liquid in 50 ml. of acetic acid is added portionwise during a 20 minute period. The reaction mixture is stirred at 65 C. for 3 hours and is cooled to 4 C. The precipitate is collected and washed with 100 ml. of ethyl acetate. The solid is suspended in 500 ml. of water, 25 ml. of concentrated ammonium hydroxide is added and the mixture is stirred at room temperature overnight. The precipitate is collected, washed with 500 ml. of water and dried at 60 C. to afford 6-(p-chlorophenyl)-3(2H)-pyridazinone.
	In water; acetic acid; ethyl acetate;	Example 16 Preparation of 6-(p-chlorophenyl)-3-methyl-1,2,4-triazolo[4,3-b]pyridazine A 47.5 g. portion of 6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone (prepared as in Example 1 of U.S. Pat. No. 3,689,652) is dissolved in 250 ml. of glacial acetic acid at 65-70 C with stirring. Then a solution of 14 ml. (42 g.) of bromine liquid in 50 ml. of acetic acid is added portionwise during a 20 minute period. The reaction mixture is stirred at 65 C. for 3 hours and is cooled to 4 C. The precipitate is collected and washed with 100 ml. of ethyl acetate. The solid is suspended in 500 ml. of water, 25 ml. of concentrated ammonium hydroxide is added and the mixture is stirred at room temperature overnight. the precipitate is collected, washed with 500 ml. of water and dried at 60 C. to afford 6-(p-chlorophenyl)-3(2H)-pyridazinone.

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CAS No.: 1079-73-8

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CAS No.: 1079-73-8

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H220	Extremely flammable gas
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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