6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one: FAQs & Properties
6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one: FAQs & Properties
6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is a bicyclic lactam building block bearing a free primary aromatic amine at the 6-position and an N-methyl substituent, making it a versatile intermediate for medicinal chemistry and heterocyclic synthesis.
- IUPAC Name
- 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one
- Aladdin SKU
- A730228
- Core Scaffold
- 3,4-Dihydroquinolin-2(1H)-one (dihydroquinolinone lactam)
- Key Functional Groups
- Primary aromatic amine (–NH₂) at C-6; N-methyl lactam carbonyl
- Molecular Formula
- C₁₀H₁₂N₂O
- Typical Application
- Synthetic intermediate and scaffold in medicinal chemistry, drug discovery, and heterocyclic chemistry research
What Is 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one?
6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is a bicyclic organic compound consisting of a partially saturated six-membered lactam ring fused to a benzene ring. The lactam nitrogen bears a methyl group (N-methyl substitution), while a primary amino group (–NH₂) is located at the 6-position of the aromatic ring. Its molecular formula is C₁₀H₁₂N₂O.
The compound belongs to the dihydroquinolinone family of heterocycles, which are well-recognized scaffolds in pharmaceutical and agrochemical research. The combination of a nucleophilic aromatic amine and a reactive lactam carbonyl within the same molecule provides two distinct handles for further chemical elaboration, making this compound a dual-functional building block.
Physical and Chemical Properties
As a solid aromatic amine lactam, 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is typically handled as a powder at ambient conditions. The aromatic amine group confers moderate basicity and strong nucleophilicity, while the lactam carbonyl is susceptible to nucleophilic acyl substitution under appropriate conditions. The N-methyl group prevents N–H tautomerism of the lactam nitrogen, locking the carbonyl in a fixed configuration.
The compound is expected to be soluble in polar aprotic solvents such as DMSO and DMF, and moderately soluble in lower alcohols. Aqueous solubility is limited due to the lipophilic bicyclic core. Researchers should consult the Certificate of Analysis (CoA) supplied with each lot for confirmed purity, melting point, and spectroscopic data.
Storage, Handling, and Safety
Aromatic amine compounds should be handled with appropriate personal protective equipment (PPE), including nitrile gloves, a laboratory coat, and eye protection. Work should be conducted in a well-ventilated area or fume hood. As with many primary aromatic amines, potential mutagenicity or sensitization cannot be excluded without specific toxicological data; consult the Safety Data Sheet (SDS) before use.
For storage, the compound should be kept in a tightly sealed container away from light, heat, moisture, and oxidizing agents. Storage at 2–8 °C under inert atmosphere is commonly recommended for amino-lactam building blocks to prevent oxidation of the amine functionality. Verify specific storage conditions on the product label and CoA provided by Aladdin Scientific.
Research Applications and Synthetic Utility
The dihydroquinolinone scaffold is a privileged structure frequently encountered in bioactive natural products and pharmaceutical agents. 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is primarily used as a synthetic intermediate in medicinal chemistry programs. The 6-amino group can participate in acylation, sulfonylation, reductive amination, condensation with carbonyls, and transition-metal-catalyzed cross-coupling reactions, enabling rapid diversification of the scaffold.
Researchers engaged in fragment-based drug discovery, kinase inhibitor programs, or the synthesis of fused polycyclic heterocycles may find this compound a valuable starting material. The lactam carbonyl also offers opportunities for ring-opening or further cyclization to access more complex architectures. The N-methyl group improves metabolic stability relative to unprotected NH analogues, a consideration relevant in early-phase drug design.
Ordering and Quality Assurance
6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is available from Aladdin Scientific under SKU A730228. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity, purity, and key physical data. Researchers requiring specific purity grades or custom pack sizes are encouraged to contact Aladdin Scientific's technical support team.
To place an order, visit the Aladdin Scientific website, search by SKU A730228 or the compound name, and follow the standard purchasing workflow. Bulk or custom synthesis inquiries can be directed to the sales team. Aladdin Scientific's quality management processes are designed to ensure batch-to-batch consistency for reliable research outcomes.
Frequently asked questions
What is the molecular formula and molecular weight of 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one?
The molecular formula of 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is C₁₀H₁₂N₂O. The corresponding molecular weight is approximately 176.21 g/mol. Please confirm the exact value against the Certificate of Analysis for the specific lot purchased.
What solvents are recommended for dissolving 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one?
Polar aprotic solvents such as DMSO and DMF are generally recommended for dissolving aromatic amine lactam building blocks of this type, as they offer good solvation of both the amine and carbonyl functionalities. Moderate solubility may also be achieved in lower alcohols such as methanol or ethanol. Aqueous solubility is expected to be limited; solubility screening under your specific assay conditions is advised.
How should 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one be stored to maintain stability?
The compound should be stored in a tightly sealed container, protected from light, heat, and moisture, and kept away from oxidizing agents. Storage at 2–8 °C under an inert atmosphere is generally recommended for primary aromatic amine compounds to minimize oxidative degradation. Always refer to the specific storage instructions on the product label and CoA provided by Aladdin Scientific.
What are the main chemical reactions accessible through the 6-amino group of this compound?
The primary aromatic amine at the 6-position is a versatile nucleophile that can undergo acylation (amide bond formation), sulfonylation, reductive amination, Schiff base condensation with aldehydes or ketones, and transition-metal-catalyzed cross-coupling reactions such as Buchwald–Hartwig amination. These transformations make the compound a useful diversification point for building compound libraries in drug discovery programs.
What is the Aladdin Scientific SKU for 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one?
6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one is listed under SKU A730228 at Aladdin Scientific. You can search by this SKU or by the full compound name on the Aladdin Scientific website to access product details, pricing, and availability.
References
- Aladdin Scientific Product Listing: 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one, SKU A730228.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, 5th ed. General reference for aromatic amine reactivity and lactam chemistry.
- Méndez-Lucio, O. et al. Dihydroquinolinone scaffolds in medicinal chemistry — a general reference for the privileged scaffold class (specific publication details to be verified).
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