2166-13-4|6-(4-Chlorophenyl)pyridazin-3(2H)-one| Ambeed

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Quality Control of [ 2166-13-4 ] Purity: 98% SDS Specification

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Product Details of [ 2166-13-4 ]

CAS No. :	2166-13-4
Formula :	C₁₀H₇ClN₂O
M.W :	206.63
SMILES Code :	O=C1C=CC(C2=CC=C(Cl)C=C2)=NN1
MDL No. :	MFCD02676708
InChI Key :	HALBJPGFCUGLFM-UHFFFAOYSA-N
Pubchem ID :	689085

Safety of [ 2166-13-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 2166-13-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2166-13-4 ]

[ 2166-13-4 ] Synthesis Path-Downstream 1~35

1
[ 1079-73-8 ]
[ 2166-13-4 ]

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].

References: [1]Synthesis,1995,p. 1240 - 1242.
[2]Journal of the American Chemical Society,1953,vol. 75,p. 1117.
[3]Patent: US5552409,1996,A .
[4]Pharmacological Reports,2019,vol. 71,p. 1253 - 1263.

2
[ 50-00-0 ]
[ 2166-13-4 ]
[ 344561-17-7 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1144 - 1149.

3
[ 2166-13-4 ]
[ 591-51-5 ]
[ 75616-15-8 ]

References: [1]Synthesis,1980,p. 457 - 460.

4
[ 2166-13-4 ]
[ 107-13-1 ]
[ 73402-22-9 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 975 - 982.

5
[ 2166-13-4 ]
[ 58059-29-3 ]

References: [1]Synthetic Communications,1986,vol. 16,p. 543 - 546.
[2]Journal of Medicinal Chemistry,1987,vol. 30,p. 239 - 249.
[3]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1202 - 1206.

6
[ 99-91-2 ]
[ 298-12-4 ]
[ 2166-13-4 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Glyoxylic acid (0.05 mol) and (0.15 mol) acetophenone derivative (nonsubstituted/4-methoxy/ 4-chloroacetophenone derivatives) were heated at 100-105 C for 2h. At the end of this period, the reaction mixture was cooled to room temperature and then, 20 ml water and 5 ml ammonium hydroxide solution (25%) were added to the reaction mixture until the medium pH became 8. Then, reaction mixture was extracted with dichloromethane (4 x 25 ml), then hydrazine hydrate (0.05 mol) was added to the separated aqueous layer and the reaction mixture was refluxed for 2h. After completion of the reaction, reaction mixture was cooled to room temperature. The resulting precipitate was filtered to give compounds 1 (mp 201-202 C; lit [19]:202-203 C), 2 (mp 190-191 C; lit [19]:188-191 C), 3 (mp 270-271 C; lit[19]:271-272 C), respectively.
		General procedure: Glyoxylic acid (0.05 mol) and 4-chloro/bromo/methylacetophe-none (0.15 mol) were heated at 100-105 C for 2 h. At the end ofthis period, the reaction mixture was cooled to 40 C and 25%ammonium hydroxide solution was added to the reaction mixtureuntil the pH of the medium reached 8. Then, the reaction mixturewas extracted with dichloromethane (20 ml), the aqueous layerwas separated and refluxed in the presence of hydrazine hydrate(0.05 mol) for 2 h. After the completion of the reaction, the mixturewas cooled to room temperature. The resulting precipitate wasfiltered to give compounds C1-3 [39-41].

References: [1]Synthesis,1993,p. 334 - 342.
[2]Medicinal Chemistry Research,2013,vol. 22,p. 2553 - 2560.
[3]Letters in drug design and discovery,2013,vol. 10,p. 507 - 514.
[4]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1202 - 1206.
[5]Pharmacological Reports,2019,vol. 71,p. 1253 - 1263.

7
[ 147674-75-7 ]
[ 2166-13-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 477 - 482.
[2]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 477 - 482.

8
[ 147674-76-8 ]
[ 2166-13-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 477 - 482.

Yield	Reaction Conditions	Operation in experiment
		...d at room temperature for 2 hours and worked up in the customary manner and 2-(1,3-benzodioxol-5-yl)-2-(2,3-dihydro-4,6-dimethylpyridazin-3-on-2-yl)N-(4-isopropylphenylsulfonyl)acetamide is obtained, m.p. 105. Analogously, by reaction of methyl benzo[1,3]dioxol-5-ylbromoacetate with ... 6-(4-methoxyphenyl)-2,3-dihydropyridazin-3-one 6-(4-chlorophenyl)-2,3-dihydropyridazin-3-one 6-(4-methoxycarbonylphenyl)-2,3-dihydropyridazin-3-one ...
		The dihydro-3(2H)-pyridazinone compounds set forth in Example 1 are dehydrogenated to the corresponding 3(2H)-pyridazinone compounds by the bromination-dehydrobromination procedure set forth in L. Pitarch, R. Coronas and J. Mallol, Eur. J. Med. Chem., Clinica Therapeutica, 9, 644, (1974). 1. 6-phenyl-3(2H)-pyridazinone 2. 6-(4-fluorophenyl)-3(2H)-pyridazinone 3. 6-(4-chlorophenyl)-3(2H)-pyridazinone 4. 6-(3,4-dichlorophenyl)-3(2H)-pyridazinone 5. 6-(3,4-dimethoxyphenyl)-3(2H)-pyridazinone 6. 6-(3,4-dihydroxyphenyl)-3(2H)-pyridazinone 7. 6-(4-methylphenyl)-3(2H)-pyridazinone 8. 6-(4-phenoxyphenyl)-3(2H)-pyridazinone 9. 6-(4-acetamidophenyl)-3(2H)-pyridazinone ...

11
[ 2166-13-4 ]
3-[3-(4-Chloro-phenyl)-6-oxo-6H-pyridazin-1-yl]-thiopropionamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 975 - 982.

12
[ 2166-13-4 ]
[ 105538-26-9 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 239 - 249.

13
[ 2166-13-4 ]
[ 58059-47-5 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 239 - 249.

14
[ 2166-13-4 ]
[ 60478-25-3 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 239 - 249.
[2]Patent: US4092311,1978,A .

15
β-(4-chlorobenzoyl)acrylic acid [ No CAS ]
[ 2166-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine monohydrate; for 3h;Reflux;	General procedure: 4.6 g (1 equivalent) ofglyoxalic acid monohydrate and 2 equivalent of substituted ace-tophenone derivative were refluxed for 4 h at 120C. After wait-ing to come to room temperature, 5 ml of ammonium hydroxide(NH 4 OH) and 25 ml of water were added. It is then extracted with4a different solvent. The aqueous-ammonia phase was isolated and0.05 mole 2.43 ml (1 equivalent) of hydrazine hydrate was addedand the reaction medium was heated under reflux for 3 h. The ob-tained solid was filtered offand crystallized

References: [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 477 - 482.
[2]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 477 - 482.
[3]Journal of Molecular Structure,2022,vol. 1261.

16
[ 2166-13-4 ]
[ 344561-16-6 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1144 - 1149.

17
[ 2166-13-4 ]
[ 85162-75-0 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1144 - 1149.

18
[ 2166-13-4 ]
[ 79460-58-5 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1144 - 1149.

19
[ 2166-13-4 ]
[ 79460-54-1 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1144 - 1149.

20
[ 2166-13-4 ]
[ 70391-14-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; diphosphorus pentasulfide;	a. 6-(4-chlorophenyl)-pyridazinthione A mixture of 3.0 g of 6-(4-chlorophenyl)-pyridazinone, 50 ml of dry pyridine and 3.2 g of phosphorus pentasulfide was refluxed for 1 hour, evaporated to dryness and extracted with 200 ml of ether. The ether extract was washed with water (3*100 ml), brine (100 ml), dried over magnesium sulfate and evaporated to yield 3.0 g of 6-(4-chlorophenyl)-pyridazinthione as a yellow solid.

References: [1]Patent: US5552409,1996,A .

21
[ 3984-34-7 ]
[ 2166-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine; In ethanol;	6-(4-Chlorophenyl)pyridazin-3-one Hydrazine (8.9 mL, 0.28 mol) was added to a suspension of 3-(4-chlorobenzoyl)propionic acid (30.0 g, 0.14 mol) in EtOH. The resulting mixture was heated to reflux for 1 hour, stirred at room temperature overnight and chilled with an ice bath. The title compound precipitated out of this mixture (23.85 g, 81%) as a yellow solid: mp 175-176 C. The following pyridazin-3-ones listed in Table 1 were prepared essentially by the above procedure, using the appropriate starting materials.

References: [1]Patent: US5684151,1997,A .
[2]Pharmacological Reports,2019,vol. 71,p. 1253 - 1263.

22
[ 1336-21-6 ]
[ 1079-73-8 ]
[ 2166-13-4 ]

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.

References: [1]Patent: US4117130,1978,A .
[2]Patent: US4112095,1978,A .

23
[ 2166-13-4 ]
[ 1079-73-8 ]
[ 58059-29-3 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; trichlorophosphate; In acetic acid;	EXAMPLE 5 Preparation of Intermediate 6-(p-chlorophenyl)-3-chloropyridazine A 283 g. portion of 6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone (prepared as described in Example 1 of U.S. Pat. No. 3,689,652) is suspended in 2500 ml. of acetic acid at room temperature with stirring. A 227 g. (72.7 ml.) portion of bromine is dissolved in 300 ml. of acetic acid and 20% of this solution is added to the reaction mixture which is then heated on a steam bath until the bromine color disappears. The balance of the bromine solution is added portionwise, over a 1/2 hour period to the heated solution. The reaction mixture is heated for an additional hour and then poured into crushed ice. The resulting solid is recovered by filtration, washed with water and dried yielding an off-white solid, m.p. 269-272 C., <strong>[2166-13-4]6-(p-chlorophenyl)-3(2H)-pyridazinone</strong>. A 269 g. portion of <strong>[2166-13-4]6-(p-chlorophenyl)-3(2H)-pyridazinone</strong> and 1500 ml. of phosphorus oxychloride are heated on a steam bath for 5 hours. The excess phosphorus oxychloride is removed under vacuum. The solid concentrate is diluted with ice water and the resulting solid is recovered by filtration, washed with water and dried. This product is recrystallized twice from dimethylformamide-water yielding 6-(p-chlorophenyl)-3-chloropyridazine as an off-white solid, m.p. 202-204 C.

References: [1]Patent: US4092311,1978,A .

24
[ 2166-13-4 ]
[ 619-23-8 ]
[ 923101-67-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;Product distribution / selectivity;	EXAMPLE 3; The preparation of 3-dimethylaminopropyl {3-[3-(4-chlorophenyl)-6-oxo-6Hpyridazin-1-ylmethyl]phenyl}carbamate (“A15”) is carried out analogously to the following scheme 3.1 1.56 g (4.79 mmol) of caesium carbonate are added to a solution of 900 mg (4.36 mmol) of 6-(4-chlorophenyl)-2H-pyridazin-3-one and 747 mg (4.36 mmol) of 3-nitrobenzyl chloride in 9 ml of DMF, and the resultant suspension is stirred at room temperature for 18 hours. Water is added to the reaction mixture, which is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate and evaporated: 6-(4-chlorophenyl)-2-(3-nitrobenzyl)-2H-pyridazin-3-one as brownish solid; ESI 342.

References: [1]Patent: US2008/293719,2008,A1 .Location in patent: Page/Page column 22; 24-25.

25
[ 2166-13-4 ]
[ 939773-32-7 ]
[ 939773-31-6 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	EXAMPLE 2; The preparation of ethyl {3-[3-(4-chlorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}carbaminate (“A3”) is carried out analogously to the following scheme 179 mg (0.55 mmol) of caesium carbonate are added to a solution of 103 mg (0.50 mmol) of 6-(4-chlorophenyl)-2H-pyridazin-3-one and 107 mg (0.50 mmol) of ethyl (3-chloromethylphenyl)carbamate [prepared from 3-aminobenzyl alcohol by reaction with ethyl chloroformate/pyridine in dichloromethane and subsequent reaction of the resultant ethyl (3-hydroxymethylphenyl)carbamate with thionyl chloride in dichloromethane] in 1 ml of dimethylformamide, and the mixture is stirred at room temperature for 18 hours. Water is added to the reaction mixture, and the resultant pre-cipitate is filtered off with suction, washed with water and dried. The crude product is recrystallised from acetonitrile: ethyl {3-[3-(4-chlorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}carbamate (“A3”) as colourless crystals; ESI 384;1H-NMR (d6-DMSO): δ=1.22 (t, J=7.3 Hz, 3H), 4.10 (q, J=7.3 Hz, 2H), 5.28 (s, 2H), 6.97 (d, J=7.8 Hz, 1H), 7.10 (d, J=10 Hz, 1H), 7.24 (t, J=8 Hz, 1H), 7.39 (d, J=9 Hz, 1H), 7.47 (bs, 1H), 7.55 (d, J=8.5 Hz, 2H), 7.93 (J=8.5 Hz, 2H), 8.08 (d, J=10 Hz, 1H), 9.58 (s, 1H).

References: [1]Patent: US2008/293719,2008,A1 .Location in patent: Page/Page column 21-22.

26
[ 452086-24-7 ]
[ 2166-13-4 ]
1-ethyl-2-(3-(4-chlorophenyl)-pyridaz-6-on-1-yl)-cyclopropene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		c. 1-Ethyl-2-(3-(4-chlorophenyl)-pyridaz-6-on-1-yl)-cyclopropene To a suspension of sodium hydride (60% in oil, 0.08 g, 2 mmol) in N,N-dimethylformamide (4 ml) in an ice bath is added 3-(4-chlorophenyl)-pyridaz-6-one (0.41 g, 2 mmol.) After stirring for 15 minutes, 1-(methanesulfonyloxymethyl)-2-ethylcyclopropene (0.35 g, 2 mmol) is added. After stirring for 45 minutes at room temperature, water and ethyl acetate were added. The phases were separated. The isolated organic layer was washed sequentially with water and brine then dried over magnesium sulfate and finally dried in vacuo. This residue was purified by column chromatography in silica gel using hexanes/ethyl acetate to give 340 mg of 1-ethyl-2-(3-(4-chlorophenyl)-pyridaz-6-on-1-yl)-cyclopropene as an off-white solid.

References: [1]Patent: US2005/65033,2005,A1 .Location in patent: Page/Page column 19.

27
[ 2166-13-4 ]
[ 144-48-9 ]
[ 86894-59-9 ]