4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one HCl Guide
4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one HCl Guide
4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride is a synthetic heterocyclic building block featuring a dihydroquinolinone scaffold with a primary aminomethyl handle and a methoxy substituent, making it a versatile intermediate for medicinal chemistry and drug discovery programmes.
- Product Name
- 4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride
- SKU
- A191183
- Core Scaffold
- 3,4-Dihydroquinolin-2(1H)-one (dihydroquinolinone)
- Key Functional Groups
- Primary aminomethyl (-CH2NH2·HCl) at C-4; methoxy (-OCH3) at C-7; lactam carbonyl
- Salt Form
- Hydrochloride salt (improves aqueous solubility and stability)
- Primary Use
- Medicinal chemistry building block; fragment-based drug design; synthesis of bioactive heterocycles
- Supplier
- Aladdin Scientific
Chemical Identity and Structural Features
4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride (Aladdin SKU A191183) belongs to the dihydroquinolinone family of bicyclic lactams. The compound consists of a partially saturated six-membered lactam ring fused to a benzene ring. Three chemically important features define its reactivity profile:
- Aminomethyl group at C-4: The primary amine is presented as its hydrochloride salt, stabilising the free base during storage and handling. Upon neutralisation, the free amine serves as a versatile nucleophile suitable for acylation, reductive amination, urea/sulfonamide formation, and imine condensation reactions.
- Methoxy substituent at C-7: The electron-donating methoxy group on the aromatic ring modulates the electronic density of the scaffold and can influence binding interactions in target engagement, particularly with enzymes that possess hydrophobic or aromatic binding pockets.
- Lactam carbonyl: The endocyclic amide carbonyl provides a hydrogen-bond acceptor and is relevant to conformational rigidity of the scaffold, contributing to favourable drug-likeness metrics such as reduced rotatable bond count.
The stereogenic centre at C-4 means the compound may exist as a racemate unless specifically resolved; researchers should confirm the stereochemical composition with the supplier's certificate of analysis before use in enantioselective studies.
Recommended Handling, Storage and Safety Protocols
Although 4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride is a research reagent rather than a classified hazardous substance at typical laboratory quantities, standard good laboratory practice (GLP) precautions should be observed:
- Personal protective equipment (PPE): Wear nitrile gloves, a laboratory coat, and safety glasses when weighing or transferring the compound. A dust mask or fume hood is recommended during powder handling to avoid inhalation of fine particulates.
- Storage conditions: Store the compound in a tightly sealed container, in a cool, dry location away from direct light. Refrigeration (2–8 °C) is generally appropriate for long-term storage of hydrochloride salts of primary amines to minimise oxidative degradation and hygroscopic uptake. Allow the container to equilibrate to room temperature before opening to prevent moisture condensation on the powder.
- Solubility and reconstitution: As a hydrochloride salt, the compound typically exhibits improved aqueous solubility relative to the free base. Stock solutions may be prepared in water, aqueous buffer, or DMSO depending on the downstream assay requirements. Prepare fresh solutions where possible; if stock solutions must be stored, aliquot to avoid freeze-thaw cycling.
- Waste disposal: Dispose of residues and solutions in accordance with institutional chemical waste management policies and applicable local regulations.
Always consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for product-specific hazard classifications, first-aid measures, and disposal guidance prior to use.
Applications in Medicinal Chemistry and Synthesis
The 3,4-dihydroquinolin-2(1H)-one (dihydroquinolinone) scaffold is a privileged structure in medicinal chemistry, appearing in a variety of pharmacologically active compounds. The aminomethyl and methoxy functional handles of A191183 make it particularly attractive for the following synthetic strategies:
- Amide and sulfonamide coupling: The primary amine can be coupled with carboxylic acids (using standard peptide coupling reagents such as HATU, EDC/HOBt) or sulfonyl chlorides to generate structurally diverse amide and sulfonamide libraries for biological screening.
- Reductive amination: Condensation with aldehydes or ketones under reductive conditions (e.g., sodium cyanoborohydride or sodium triacetoxyborohydride) provides secondary and tertiary amine derivatives with expanded structural diversity.
- Urea and carbamate formation: Reaction with isocyanates or chloroformates yields urea and carbamate analogues, motifs frequently encountered in kinase inhibitors and protease inhibitors.
- Fragment-based drug design (FBDD): The compact, rigid bicyclic core with defined hydrogen-bond donor/acceptor capacity makes this compound suitable as a fragment hit or a fragment elaboration starting point in FBDD campaigns targeting enzymes and receptors.
- Scaffold hopping: The dihydroquinolinone core can serve as a bioisostere for related lactam and benzamide scaffolds, facilitating intellectual property diversification in lead optimisation programmes.
Researchers are encouraged to confirm compound purity via HPLC and identity via NMR or HRMS prior to incorporation into key synthetic steps or biological assays.
Quality Assurance and Ordering Information
Aladdin Scientific provides 4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride under SKU A191183. When procuring this reagent, consider the following quality and ordering checkpoints:
- Certificate of Analysis (CoA): Request the batch-specific CoA to confirm identity (NMR, MS), purity (HPLC), and appearance. Verify that the purity specification meets your application requirements before use in quantitative assays.
- Quantity and packaging: Contact Aladdin Scientific's technical sales team to enquire about available pack sizes, pricing tiers, and lead times, particularly for larger quantities required in library synthesis or scale-up campaigns.
- Custom synthesis: If a specific enantiomer, isotopically labelled analogue, or derivative is required, enquire about Aladdin Scientific's custom synthesis services.
- Regulatory documentation: For regulated research environments, request SDS, export control classification, and any available TSE/BSE declarations as required by your institution's compliance framework.
For technical enquiries regarding this compound, contact Aladdin Scientific's scientific support team, referencing SKU A191183.
Frequently asked questions
What is the recommended solvent for preparing stock solutions of A191183?
As a hydrochloride salt, 4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride generally shows good solubility in water and aqueous buffers. DMSO is a suitable alternative for applications requiring an organic co-solvent. The optimal solvent should be confirmed empirically for each specific assay format, and researchers should verify that the chosen solvent is compatible with downstream biological or chemical reactions.
Is A191183 available as a single enantiomer?
The compound possesses a stereogenic centre at C-4, and the standard catalogue offering may be a racemic mixture. Researchers requiring a specific enantiomer should contact Aladdin Scientific directly to enquire about chiral separation or asymmetric synthesis options through the custom synthesis service. Always verify stereochemical composition from the batch certificate of analysis.
What coupling reactions are most suitable for functionalising the aminomethyl group of A191183?
The primary aminomethyl group (after neutralisation of the HCl salt with a mild base such as triethylamine or DIPEA) is compatible with standard amide bond-forming reactions using HATU, EDC/HOBt, or similar coupling reagents. Sulfonamide formation with sulfonyl chlorides, reductive amination with aldehydes/ketones, and urea formation with isocyanates are all well-established routes. Reaction conditions should be optimised and the product confirmed by analytical techniques such as LC-MS before proceeding to scale.
How should I store A191183 to maximise shelf life?
Store the compound in a tightly sealed container at 2–8 °C in a dry, dark environment. Allow the vial to warm to room temperature before opening to prevent moisture absorption. Avoid repeated exposure to air and humidity, as primary amine hydrochloride salts can be hygroscopic. Adhere to the expiry date and storage conditions stated on the product label and CoA.
References
- Aladdin Scientific product page and Certificate of Analysis for SKU A191183: 4-(Aminomethyl)-7-methoxy-3,4-dihydroquinolin-2(1H)-one hydrochloride.
- Küenburg, B. et al. Development of a Privileged Structure: From Dihydroquinolinones to Drug Candidates — a general reference on dihydroquinolinone scaffold utility in medicinal chemistry (representative literature; specific citation to be confirmed).
- Roughley, S. D.; Jordan, A. M. The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates. J. Med. Chem. 2011, 54, 3451–3479. doi:10.1021/jm200187y
- Erlanson, D. A.; Fesik, S. W.; Hubbard, R. E.; Jahnke, W.; Jhoti, H. Twenty years on: the impact of fragments on drug discovery. Nat. Rev. Drug Discov. 2016, 15, 605–619. doi:10.1038/nrd.2016.109
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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