1-(5-chloro-2-nitrophenyl)hydrazine -Drug Synthesis Database

【结构式】

【分子编号】35819

【品名】1-(5-chloro-2-nitrophenyl)hydrazine

【CA登记号】

【分子式】C₆H₆ClN₃O₂

【分子量】187.58536

【元素组成】C 38.42% H 3.22% Cl 18.9% N 22.4% O 17.06%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

Condensation of 2-nitro-5-chlorophenylhydrazine (I) with cyanoaldehyde (II) afforded the aminopyrazole derivative (III). This was then cyclized to the target benzotriazine system upon treatment with aqueous NaOH.

参考文献中间体

合成目标

【1】 Bruni, F.; Malmberg Aiello, P.; Guerrini, G.; Martini, C.; Ipponi, A.; Costanzo, A.; Ciciani, G.; Costa, B.; Luccchini, A.; Selleri, S.; Benzodiazepine receptor ligands. 4. Synthesis and pharmacological evaluation of 3-heteroaryl-8-chloropyrazolo[5,1-c][1,2, 4]benzotriazine 5-oxides. J Med Chem 1999, 42, 12, 2218.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	35819	1-(5-chloro-2-nitrophenyl)hydrazine	C₆H₆ClN₃O₂	详情	详情
(II)	35820	3-oxo-2-(3-thienyl)propanenitrile	C₇H₅NOS	详情	详情
(III)	35821	1-(5-chloro-2-nitrophenyl)-4-(3-thienyl)-1H-pyrazol-5-amine; 1-(5-chloro-2-nitrophenyl)-4-(3-thienyl)-1H-pyrazol-5-ylamine	C₁₃H₉ClN₄O₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Reaction of 2-nitro-5-chlorophenylhidrazyne (I) with ethyl 2-cyano-3-ethoxypropenoate (II) in EtOH and catalytic HOAc affords derivative (III), which is simultaneously hydrolyzed and cyclized to the triazine system (IV) in aqueous NaOH. Treatment of (IV) with SOCl2 followed by addition of alcohol (V) in chloroform allows obtention of the desired product.

参考文献中间体

合成目标

【1】 Costanzo, A.; et al.; Reactivity of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions and synthesis of new 3,7 and 8-substituted pyrazole[5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands. J Heterocycl Chem 1994, 31, 1369.
【2】 Costa, B.; Ciciani, G.; Costanzo, A.; Ipponi, A.; Martini, C.; Bruni, F.; Guerrini, G.; Selleri, S.; Lucacchini, A.; Aiello, M.; Benzodiazepine receptor (BZR) ligands.5. New 3-alkyloxycarbonyl-, 3-cyclo-alkyloxycarbonyl-, 3-aryloxy-carbonylderivatives of pyrazolo [5,1-c][1,2,4]benzotriazine 5-oxides: A study on the 3-ester function modification. Med Chem Res 1999, 9, 5, 322.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	35819	1-(5-chloro-2-nitrophenyl)hydrazine		C₆H₆ClN₃O₂	详情	详情
(II)	43041	ethyl (Z)-2-cyano-3-ethoxy-2-propenoate	94-05-3	C₈H₁₁NO₃	详情	详情
(III)	43042	ethyl 5-amino-1-(5-chloro-2-nitrophenyl)-1H-pyrazole-4-carboxylate		C₁₂H₁₁ClN₄O₄	详情	详情
(IV)	43043	3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-5-olate		C₁₀H₅ClN₄O₃	详情	详情
(V)	16664	Propargyl Alcohol; 2-propyn-1-ol	107-19-7	C₃H₄O	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

Reaction of 2-nitro-5-chlorophenylhidrazyne (I) with ethyl 2-cyano-3-ethoxypropenoate (II) in EtOH and catalytic AcOH affords derivative (III), which is simultaneously hydrolyzed and cyclized to the triazine system (IV) in aqueous NaOH. Treatment of (IV) with SOCl2, followed by addition of alcohol (V) in chloroform, allows obtention of the desired product.

参考文献中间体

合成目标

【1】 Costanzo, A.; et al.; Reactivity of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions and synthesis of new 3,7 and 8-substituted pyrazole[5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands. J Heterocycl Chem 1994, 31, 1369.
【2】 Costa, B.; Ciciani, G.; Costanzo, A.; Ipponi, A.; Martini, C.; Bruni, F.; Guerrini, G.; Selleri, S.; Lucacchini, A.; Aiello, M.; Benzodiazepine receptor (BZR) ligands.5. New 3-alkyloxycarbonyl-, 3-cyclo-alkyloxycarbonyl-, 3-aryloxy-carbonylderivatives of pyrazolo [5,1-c][1,2,4]benzotriazine 5-oxides: A study on the 3-ester function modification. Med Chem Res 1999, 9, 5, 322.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	35819	1-(5-chloro-2-nitrophenyl)hydrazine		C₆H₆ClN₃O₂	详情	详情
(II)	43041	ethyl (Z)-2-cyano-3-ethoxy-2-propenoate	94-05-3	C₈H₁₁NO₃	详情	详情
(III)	43042	ethyl 5-amino-1-(5-chloro-2-nitrophenyl)-1H-pyrazole-4-carboxylate		C₁₂H₁₁ClN₄O₄	详情	详情
(IV)	43043	3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-5-olate		C₁₀H₅ClN₄O₃	详情	详情
(V)	18710	Benzyl alcohol; Phenylmethanol	100-51-6	C₇H₈O	详情	详情

Extended Information