4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide

Base Information

• Chemical Name: 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide
• CAS No.: 873942-91-7
• Molecular Formula: C₁₁H₈F₃N₃O₂
• Molecular Weight: 271.199
• Mol file: 873942-91-7.mol

Synonyms:4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide

Chemical Property of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide

There total 4 articles about 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.6%

4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (23851-84-5) → 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide (873942-91-7)

Guidance literature:

With hydrazine; In ethanol; for 4h; Reflux;

DOI:10.1016/j.ejmech.2013.07.021

Reference yield:

2-(trifluoromethyl)benzenamine (88-17-5) → 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide (873942-91-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 4 h / 110 °C

2: Dowtherm medium / 4 h / 250 °C

3: hydrazine hydrate / ethanol / 2.5 h / Reflux

With hydrazine hydrate; In ethanol; Dowtherm medium;

DOI:10.1016/j.ejmech.2011.07.033

Reference yield:

2-[(2-trifluoromethylphenylamino)methylene]malonic acid diethyl ester (23779-94-4) → 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide (873942-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Dowtherm medium / 4 h / 250 °C

2: hydrazine hydrate / ethanol / 2.5 h / Reflux

With hydrazine hydrate; In ethanol; Dowtherm medium;

DOI:10.1016/j.ejmech.2011.07.033

upstream raw materials:

4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester

2-[(2-trifluoromethylphenylamino)methylene]malonic acid diethyl ester

2-(trifluoromethyl)benzenamine

4-hydroxy-8-(trifluoromethyl)quinoline-3-carboxylic acid

Downstream raw materials:

C₁₉H₁₅F₃N₄O₂S

C₁₈H₁₃F₃N₄O₂S

4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid (3-hydroxy-4-methoxy-benzylidene)-hydrazide

4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid (5-fluoro-2-hydroxy-benzylidene)-hydrazide

Refernces

Synthesis, identification and in vitro biological evaluation of some novel quinoline incorporated 1,3-thiazinan-4-one derivatives

10.1016/j.bmcl.2016.06.038

The study focuses on the synthesis, identification, and in vitro biological evaluation of novel quinoline-incorporated 1,3-thiazinan-4-one derivatives. Two new series of compounds, 3-hydroxy-N-(4-oxo-2-phenyl-1,3-thiazinan-3-yl)-8-(trifluoromethyl)quinoline-2-carboxamide derivatives (4a-j) and 3-((7-chloroquinolin-4-ylamino)methyl)-2-phenyl-1,3-thiazinan-4-one derivatives (5a-7j), were synthesized through a one-pot three-component cyclo-condensation reaction. These compounds were characterized using FT-IR, 1H, 13C NMR, and elemental analysis. Their in vitro biological activities were assessed for antibacterial effects against various pathogenic bacterial strains, antitubercular activity against Mycobacterium Tuberculosis H37Rv, and antimalarial activity against Plasmodium falciparum. The study identified certain compounds, particularly 4f and 5f, that exhibited excellent antibacterial and antitubercular activities, along with good antimalarial activity, comparing favorably with frontline drugs. The findings suggest potential for these compounds as new antimicrobial, antitubercular, and antimalarial agents.

Ultra-sensitive and selective Hg²⁺ chemosensors derived from substituted 8-hydroxyquinoline analogues

10.1039/c3nj01308a

The research focuses on the synthesis, identification, and in vitro biological evaluation of novel quinoline-incorporated 1,3-thiazinan-4-one derivatives. The study describes the creation of two new series of compounds, (4a-j) and (5a-7j), through a one-pot three-component cyclo-condensation reaction, yielding products in moderate to good yields. The synthesis involved reactants such as 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide, substituted benzaldehydes, 3-mercaptopropionic acid, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). The synthesized compounds were characterized using Fourier-transform infrared spectroscopy (FT-IR), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), and elemental analysis to confirm their structures. The in vitro biological evaluation involved screening the compounds for antibacterial activity against both Gram-positive and Gram-negative bacteria, antitubercular activity against Mycobacterium Tuberculosis H37Rv, and antimalarial activity against Plasmodium falciparum. The results indicated that some compounds, particularly 4f and 5f, showed excellent antibacterial and antitubercular activity, while several others demonstrated good antimalarial activity, presenting potential as new antimicrobial, antitubercular, and antimalarial agents.