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Chemistry
Heterocyclic Building Blocks
Pyrroles
4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzohydrazide
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Pyrroles
Aryls Amines Amides Hydrazines Hydrazides

[ CAS No. 26165-67-3 ] {[proInfo.proName]}

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Chemical Structure| 26165-67-3
Chemical Structure| 26165-67-3
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Product Details of [ 26165-67-3 ]

CAS No. :26165-67-3 MDL No. :MFCD01570907
Formula : C13H15N3O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.28 Pubchem ID :-
Synonyms :

Safety of [ 26165-67-3 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 26165-67-3 ]

* 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 [ 26165-67-3 ]

[ 26165-67-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 26165-66-2 ]
  • [ 26165-67-3 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine hydrate In ethanol Reflux; 3.2.4. 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide (18) A mixture of methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate (16) (2.29 g, 10 mmol) and hydrazine hydrate(2.25 g, 45 mmol) in 96% ethanol (10 mL) was heated at reflux temperature overnight. The solid that separatedon cooling was filtered and recrystallized to give colorless crystals (1.95 g, 85%), mp 164-165 °C (ethanol) (lit.35mp 148 °C); 1 H NMR (DMSO-d6 , 400 MHz): 1.97 (s, 6H), 4.54 (s, 2H, exchangeable with D), 5.81 (s, 2H),7.34 (d, J = 8.4 Hz, 2H), 7.94 (d, J = 8.4 Hz, 2H), 9.89 (s, 1H, exchangeable with D); 13 C NMR (DMSO-d6 ,100 MHz): 12.9, 106.4, 127.5, 127.8, 128.0, 132.4, 140.6, 165.2. Anal. Calcd. for C13 H15 N3 O: C, 68.10; H,6.59; N, 18.33. Found: C, 68.25; H, 6.71; N, 18.48.
With hydrazine hydrate In ethanol for 1h; Reflux;
Reference： [1]Roman, Gheorghe; Bostănaru, Andra-Cristina; Năstasă, Valentin; Mareş, Mihai [Turkish Journal of Chemistry, 2019, vol. 43, # 2, p. 531 - 546]
[2]Location in patent: experimental part Dong, Ming-Xin; Zhang, Jian; Peng, Xu-Qing; Lu, Hong; Yun, Liu-Hong; Jiang, Shibo; Dai, Qiu-Yun [European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4096 - 4103]
  • 2
  • [ 15898-26-7 ]
  • [ 26165-67-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / Reflux 2: hydrazine hydrate / Reflux
Reference： [1]More, Uttam A.; Joshi, Shrinivas D.; Aminabhavi, Tejraj M.; Gadad, Andanappa K.; Nadagouda, Mallikarjuna N.; Kulkarni, Venkatrao H. [European Journal of Medicinal Chemistry, 2014, vol. 71, p. 199 - 218]
  • 3
  • [ 26165-67-3 ]
  • [ 121-92-6 ]
  • N'-(3-nitrobenzoyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; General procedure for the synthesis of 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N’-(substituted benzoyl) benzohydrazides 4(a-j) General procedure: 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide (3) (0.0018 mol) and different substituted benzoic acids (0.39 g and 0.0019 mol) were dissolved in dry N’,N’-dimethyl formamide. HBTU (0.87 g and 0.0023 mol) and DIEA (0.93 ml and 0.0053 mol) were added, and the mixture was stirred for 24 h at room temperature. The reaction was quenched by adding brine. The resulting mixture was extracted with ethyl acetate (3 × 50 ml). The combined ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate, followed by brine. The organic layer was dried over anhydrous sodium sulfate to give titled compounds 4(a-j). The residue left after concentrating the ethyl acetate layer in vacuum was purified by column chromatography using ethyl acetate: petroleum ether (6:4) as a solvent and iodine vapors as visualizing agent.
Reference： [1]Joshi, Shrinivas D.; Vinayak; Prem Kumar; Dixit, Sheshagiri R. [Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 2, p. 195 - 200]
  • 4
  • [ 26165-67-3 ]
  • [ 99-05-8 ]
  • N'-(3-aminobenzoyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; General procedure for the synthesis of 4-(2,5-dimethyl-1H-pyrrol-1-yl)-N’-(substituted benzoyl) benzohydrazides 4(a-j) General procedure: 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide (3) (0.0018 mol) and different substituted benzoic acids (0.39 g and 0.0019 mol) were dissolved in dry N’,N’-dimethyl formamide. HBTU (0.87 g and 0.0023 mol) and DIEA (0.93 ml and 0.0053 mol) were added, and the mixture was stirred for 24 h at room temperature. The reaction was quenched by adding brine. The resulting mixture was extracted with ethyl acetate (3 × 50 ml). The combined ethyl acetate layer was washed with 1N HCl then with saturated sodium bicarbonate, followed by brine. The organic layer was dried over anhydrous sodium sulfate to give titled compounds 4(a-j). The residue left after concentrating the ethyl acetate layer in vacuum was purified by column chromatography using ethyl acetate: petroleum ether (6:4) as a solvent and iodine vapors as visualizing agent.
Reference： [1]Joshi, Shrinivas D.; Vinayak; Prem Kumar; Dixit, Sheshagiri R. [Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 2, p. 195 - 200]
  • 5
  • [ 26165-67-3 ]
  • [ 399-10-0 ]
  • C28H24FN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In ethanol for 16h; Reflux; (4-(2,5-Dimethylpyrrol-1-yl)phenyl)(5-subtitutedphenyl-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanones (5a-g): General procedure General procedure: In a mixture of appropriate chalcones (3a-g)20 (0.01 mol) in ethanol, 4-(2,5-dimethyl pyrrol-1-yl)benzoic acid hydrazide (4)21 (0.01 mol) was added in a round bottom flask. The reaction mixture was heated under reflux for 16 h on a water bath followed by addition of ice cold water at room temperature. The mixture was kept overnight at 8°C. The precipitate was filtered, washed with distilled water and dried. The crude crystals were recrystallized from ethanol.
Reference： [1]Hallikeri; Joshi, Shrinivas D.; Kulkarni [Indian Journal of Heterocyclic Chemistry, 2015, vol. 25, # 2, p. 157 - 160]

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