68304-21-2

Basic information

• Product Name: 8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde
• Synonyms: 8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde;5-ForMyl-8-hydroxycarbostyril;Indacaterol Impurity 13;8-hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde;Procaterol Impurity 11
• CAS NO: 68304-21-2
• Molecular Formula: C10H7NO3
• Molecular Weight: 189.1675
• Product Categories: Aromaitcs, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 68304-21-2.mol

Chemical Properties

• Melting Point: 315-317 °C (decomp)
• Boiling Point: 462.2°Cat760mmHg
• Flash Point: 233.3°C
• Appearance: /
• Density: 1.431g/cm³
• Vapor Pressure: 3.65E-09mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO, Methanol (Sparingly)
• PKA: 6.65±0.20(Predicted)
• CAS DataBase Reference: 8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde(68304-21-2)
• EPA Substance Registry System: 8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde(68304-21-2)

Safety Data

• Hazardous Substances Data: 68304-21-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific receptors or enzymes in the body.
Used in Chemical Research:
8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde is also utilized in chemical research for studying the properties and reactivity of quinoline derivatives. It can be used to explore new synthetic pathways and develop novel chemical reactions that could lead to the creation of new molecules with potential applications in various fields.
Used in Metabolite Studies:
As a metabolite of procaterol hydrochloride (Meptin), a β2-adrenergic agonist used in the treatment of asthma, 8-Hydroxy-2-oxo-1,2-dihydro-5-quinolinecarboxaldehyde is relevant in the study of drug metabolism and pharmacokinetics. Understanding its role in the body can provide insights into the effectiveness and safety of procaterol hydrochloride as a treatment for asthma.

InChI:InChI=1/C10H7NO3/c12-5-6-1-3-8(13)10-7(6)2-4-9(14)11-10/h1-5,13H,(H,11,14)

Upstream product

• 173140-90-4 (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone 
• 66546-38-1 8-(benzyloxy)carbostyril-5-carboxaldehyde 

Relevant articles and documents

Method for preparing 5-formyl-8-hydroxy-1, 3, 4-trihydroquinoline-2-ketone

The invention relates to a method for preparing 5-formyl-8-hydroxy-1, 3, 4-trihydroquinoline-2-ketone, and particularly relates to a method for preparing oxidative degradation impurity of procaterol. The method is easy to operate, high in yield and low in cost.

Procaterol hydrochloride impurity preparation method

The invention discloses a procaterol hydrochloride impurity preparation method, which comprises: 1, adding procaterol hydrochloride to an organic solvent under an alkaline condition, adding an appropriate amount of benzyl halide, carrying out heating reflux until the reaction is complete, and carrying out post-treatment to obtain an intermediate 1; step 2, adding the intermediate 1 into a reaction bottle, then adding an organic solvent, raising the temperature, adding an oxidant aqueous solution, pouring into ice water after heating reaction is completed, and separating out a solid to obtain an intermediate 2; and step 3, adding the intermediate 2 into a reaction bottle, then adding an organic solvent, cooling to a low temperature, slowly adding boron trichloride, keeping the low temperature until the reaction is complete, pouring into ice water, separating out solids, and filtering to obtain the procaterol impurity. Procaterol hydrochloride which is easy to obtain is used as an initial raw material to prepare the procaterol hydrochloride impurity, the synthesis cost of the procaterol hydrochloride impurity is reduced, the preparation steps of the procaterol hydrochloride impurity are simplified, and the selectivity is improved, so that the preparation time is saved, and the preparation efficiency is improved. The total yield of the reaction is 50-70%.

Kinetics of procaterol auto-oxidation in buffered acid solutions

The kinetics of procaterol (1) degradaton in buffered acidic solutions (pH 4-6) was investigated using a HPLC procedure. The effect of temperature and ferric ions on the reaction rate was estimated. In acidic solutions, 1 undergoes pseudo first-order degradation with an induction period. The first-order rate constant for degradation increased and the induction period decreased with an increase in pH. Ferric ions catalyzed the degradation reaction and decreased the induction period. At pH 6, the activation energy of the reaction was 34.5 kcal/mol/deg. The results of this study indicate that 1 in solution is more stable at acidic pH, in the absence of heavy metal ions, and protected from air.