92-99-9

Usage

Uses

Used in Pharmaceutical Synthesis:
N,N,2-trimethylquinolin-6-amine is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of novel drug candidates with potential therapeutic applications.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, N,N,2-trimethylquinolin-6-amine is utilized as a building block for the creation of diverse organic compounds, leveraging its structural features to enhance the properties of the resulting molecules.
Used in Materials Science:
N,N,2-trimethylquinolin-6-amine is employed in materials science for its potential to contribute to the development of new materials with unique properties, such as improved conductivity or stability, due to its chemical structure.
Used in Medicinal Research:
In the realm of medicinal research, N,N,2-trimethylquinolin-6-amine is used as a compound of interest for studying its biological activities and exploring its potential as a therapeutic agent, given its distinctive chemical features that may offer new avenues for treatment and intervention in various diseases.

InChI:InChI=1/C22H25BrCl2N6O/c23-17-5-7-21(29-12-17)31(14-16-4-6-19(24)20(25)11-16)10-2-9-28-22(32)27-8-1-3-18-13-26-15-30-18/h4-7,11-13,15H,1-3,8-10,14H2,(H,26,30)(H2,27,28,32)

Synthetic route

4-amino-N,N-dimethylaniline (99-98-9) + ethyl vinyl ether (109-92-2) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With iodine In benzene at 80℃; for 2h; Green chemistry;	83%

trans-Crotonaldehyde (123-73-9) + 4-amino-N,N-dimethylaniline (99-98-9) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 1h;	70%
With hydrogenchloride In water; toluene Inert atmosphere; Reflux;	62%
In toluene at 20℃;
In toluene at 20℃;

4-amino-N,N-dimethylaniline (99-98-9) + crotonaldehyde (123-73-9) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With hydrogenchloride In water	70%
With hydrogenchloride In water; toluene at 20℃;	70%
With hydrogenchloride In toluene Reflux;	65%

2-hydroxy-3-butene (598-32-3) + 4-amino-N,N-dimethylaniline (99-98-9) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Stage #1: 4-amino-N,N-dimethylaniline With acetic anhydride In tetrahydrofuran Inert atmosphere; Stage #2: 2-hydroxy-3-butene With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In tetrahydrofuran at 120℃; Inert atmosphere; Sealed tube;	65%

2-methylquinolin-6-amine (65079-19-8) + methyl iodide (74-88-4) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Stage #1: 2-methylquinolin-6-amine With sodium hydride In N,N-dimethyl-formamide at 40℃; for 3h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 40℃;	39%

C15H19N3O2 (78827-70-0) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 7-Dimethylamino-2-methyl-benzo[d][1,3]diazepine-3-carboxylic acid ethyl ester (78827-75-5)

Conditions	Yield
In benzene Irradiation;	A 32% B 26%

4-amino-N,N-dimethylaniline (99-98-9) + paracetaldehyde (123-63-7) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With hydrogenchloride

2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; (84689-24-7) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 20 percent / potassium carbonate / ethanol / 8 h / Ambient temperature 2: 32 percent / benzene / Irradiation View Scheme

N,N-Dimethyl-4-nitroaniline (100-23-2) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 0.33 h / 25 °C / 750.08 - 2250.23 Torr / Inert atmosphere 2.1: acetic anhydride / tetrahydrofuran / Inert atmosphere 2.2: 120 °C / Inert atmosphere; Sealed tube View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + methyl iodide (74-88-4) → 6-(dimethylamino)-1,2-dimethylquinolin-1-ium iodide

Conditions	Yield
Sealed tube;	100%
In ethanol at 79℃; for 12h; Sealed tube;	25.06%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; (84689-24-7)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	88%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 2-phenyl-1,2,3,4-tetrahydroisoquinoline (3340-78-1) → N,N-dimethyl-2-((2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-yl)methyl)quinoline-6-amine

Conditions	Yield
With C52H49B9CuN2P2; oxygen; m-Toluic acid In methanol; acetonitrile for 35h; Photolysis;	77%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → 6-(dimethylamino)quinoline-2-carboxaldehyde (1267631-83-3)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water at 80℃; for 4h;	58%
With selenium(IV) oxide	40%
With selenium(IV) oxide In 1,4-dioxane; water at 80℃; for 4h;	38%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + ethyl iodide (75-03-6) → C14H20N2*I(1-)

Conditions	Yield
In ethanol at 60℃; for 12h;	43.72%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-(dimethylamino)-2-methylquinoline-5-carbaldehyde

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In chloroform at 0℃; for 1h; Vilsmeier-Haack Formylation; Inert atmosphere; Stage #2: 6-(N,N-dimethylamino)-2-methylquinoline In chloroform for 16h; Vilsmeier-Haack Formylation; Reflux; Inert atmosphere;	38.6%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + methyl p-toluene sulfonate (80-48-8) → 6-dimethylamino-1,2-dimethylquinolinium tosylate (902158-30-9)

Conditions	Yield
In chloroform for 14h; Solvent; Reflux;	34%
In chloroform for 12h; Heating / reflux;

1,4-butane sultone (1633-83-6) + 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → C16H22N2O3S

Conditions	Yield
In 1,2-dichloro-benzene at 120℃; for 12h;	30.44%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (83-18-1) → N,N-Dimethyl-2-((E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)quinolin-6-amine

Conditions	Yield
Stage #1: 6-(N,N-dimethylamino)-2-methylquinoline; 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde With zinc(II) chloride In N,N-dimethyl-formamide at 160℃; Stage #2: With sodium hydroxide; water In N,N-dimethyl-formamide	2.1%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 1-iodo-butane (542-69-8) → 1-butyl-6-dimethylamino-2-methyl-quinolinium; iodide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 1-Bromoheptane (629-04-9) → 6-dimethylamino-1-heptyl-2-methyl-quinolinium; bromide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 1-Iodoheptane (4282-40-0) → 6-dimethylamino-1-heptyl-2-methyl-quinolinium; iodide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 3-(4-dimethylamino-phenyl)-propenal (20432-35-3, 6203-18-5) → 6-dimethylamino-2-[4t-(4-dimethylamino-phenyl)-buta-1,3-dien-t-yl]-quinoline

Conditions	Yield
With hydrogenchloride

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + ethyl iodide (75-03-6) → 1-ethyl-6-dimethylamino-2-methyl-quinolinium; iodide + ethyl-dimethyl-(2-methyl-[6]quinolyl)-ammonium; iodide

Conditions	Yield
at 140 - 150℃;

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + allyl bromide (106-95-6) → 1-allyl-6-dimethylamino-2-methyl-quinolinium; bromide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 4-dimethylamino-benzaldehyde (100-10-7) → [2-(4-dimethylamino-trans-styryl)-[6]quinolyl]-dimethyl-amine (36429-38-6)

Conditions	Yield
With hydrogenchloride at 120℃;

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + methyl iodide (74-88-4) → trimethyl-<2-methyl-quinolyl-(6)>-ammonium iodide + 6-dimethylamino-quinaldine iodomethylate

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + ethyl iodide (75-03-6) → ethyl-dimethyl-(2-methyl-[6]quinolyl)-ammonium; iodide + 1-ethyl-6-dimethylamino-2-methyl-quinolinium

Conditions	Yield
at 140 - 150℃;

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → 7-Dimethylamino-2-methyl-benzo[d][1,3]diazepine-3-carboxylic acid ethyl ester (78827-75-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / CH2Cl2 / 1 h / Ambient temperature 2: 20 percent / potassium carbonate / ethanol / 8 h / Ambient temperature 3: 26 percent / benzene / Irradiation View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → C15H19N3O2 (78827-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / CH2Cl2 / 1 h / Ambient temperature 2: 20 percent / potassium carbonate / ethanol / 8 h / Ambient temperature View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → (6-(dimethylamino)quinolin-2-yl)methanol (1267895-81-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: selenium(IV) oxide / water; 1,4-dioxane / 4 h / 80 °C 2: sodium tetrahydroborate / ethanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate; ethanol / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → (6-(dimethylamino)quinolin-2-yl)methyl acetate (1221541-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: selenium(IV) oxide / water; 1,4-dioxane / 4 h / 80 °C 2: sodium tetrahydroborate / ethanol / 1 h / 20 °C 3: triethylamine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere; Darkness View Scheme

Upstream product

• 99-98-9 4-amino-N,N-dimethylaniline 
• 123-63-7 paracetaldehyde 
• 78827-70-0 C₁₅H₁₉N₃O₂ 
• 65079-19-8 2-methylquinolin-6-amine 
• 74-88-4 methyl iodide 
• 123-73-9 trans-Crotonaldehyde 
• 598-32-3 2-hydroxy-3-butene 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 123-73-9 crotonaldehyde 
• 109-92-2 ethyl vinyl ether 
• 84689-24-7 2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; 

Downstream Products

• 84689-24-7 2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; 
• 902158-30-9 6-dimethylamino-1,2-dimethylquinolinium tosylate 
• 61791-77-3 (E)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl]-1-methyl-6-(dimethylamino)quinolinium methyl sulphate salt 
• 3546-41-6 pyrvinium pamoate 
• 35648-29-4 (E)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)-6-(dimethylamino)-1-methylquinolin-1-ium iodide 

Relevant academic research and scientific papers

A fluorescent sensor for selective detection of hypochlorite and its application in Arabidopsis thaliana

Hypochlorite, as one of reactive oxygen species, has drawn much attention due to its essential roles in special biological events and disorders. The exogenous hypochlorite remains a risk for human, animals and plants. In this work, a novel water soluble quinolin-containing nitrone derivative T has been developed for fluorometric sensing hypochlorite. The response mechanism of T towards ClO? was reported for the first time. In comparison with the reported sensors for ClO?, the sensor T in this work exhibited advantages including high selectivity (80 fold over other analytes), rapid response (within 5 s) and lipid-water distribution transformation (LogP from 2.979 to 6.131). Further biological applications suggested that T was capable of monitoring both exogenous and endogenous ClO? in living cells. The imaging in Arabidopsis thaliana indicated that the absorption and transmission of ClO? in plant could be monitored by this sensor through the chlorine-related mechanism. This work might raise referable information for further investigations in the physiological and pathological events in both tumor and plants.

Monitoring of Fe (II) ions in living cells using a novel quinoline-derived fluorescent probe

Physiologically, Fe(III) and Fe(II) is the most important redox pairs in a variety of biological and environmental procedures with its capability of transition. The detection of physiological iron, especially Fe(II), has become the recent research focus of investigations on revealing the mechanism of iron-related metabolism. In this work, we exploited a novel quinoline-derived fluorescent probe, YTP, for the detection of Fe(II). It could monitor the level of Fe(II) with a linear range of 0–2.0 equivalent and the detection limit of 0.16 μM. High selectivity from other analytes including Fe(III) and steadiness for over 24 h confirmed the practicability of YTP. YTP was further applied in real buffer systems and in cellular imaging. The probe could achieve the semi-quantitative monitoring of Fe(II) in living cells. This work provided a potential implement for the detection of Fe(II), and raised important information for further researches on the redox pairs of iron, in mechanism and in practice.

Imaging of formaldehyde in plants with a ratiometric fluorescent probe

The fluorescence monitoring of formaldehyde in real environmental samples and live plant tissues is of great importance for physiological and pathological studies. However, there is a lack of suitable chemical tools to directly trace and measure the formaldehyde activity in bio-systems, and developing effective and, in particular, selective sensors for mapping formaldehyde in live tissues still remains a great challenge. Here, we demonstrate for the first time that the ratiometric fluorescence monitoring of formaldehyde in live plant tissues is achieved with a newly developed ratiometric fluorescent probe, FAP, which effectively eliminated interference from other comparative analytes. Live tissue analyses reveal that FAP can potentially detect exogenous and endogenous formaldehyde in live Arabidopsis thaliana tissues, exposing a potential application for biological and pathological studies of formaldehyde.

Fluorescent probe with AIE property, preparation method and application of fluorescent probe in detection of transthyretin tetramer protein

The invention discloses a fluorescent probe with an AIE property, preparation and application of the fluorescent probe in detection of transthyretin tetramer protein. The structural formula of the fluorescent probe is shown as a formula (I). The preparation method comprises the following steps: adding 6-(dimethylamino) quinoline-2-formaldehyde, 4-aminophenylacetonitrile and tetrabutylammonium bromide into ethanol, carrying out a reflux reaction under the conditions of sealing and 80 +/-5 DEG C, cooling to room temperature after the reaction is finished, standing to separate out a solid, carrying out suction filtration, and washing to obtain the fluorescent probe with the AIE property. The fluorescent probe with the AIE property, prepared by the invention, has a fluorescence aggregation-induced emission effect, can be combined with transthyretin tetramer protein to generate stronger fluorescence, and can be used for quantitative research of transthyretin tetramer protein of an organism.

Beta-amyloid protein targeting fluorescent probe, preparation and application of beta-amyloid protein targeting fluorescent probe in Alzheimer's disease

The invention discloses a beta-amyloid protein targeting fluorescent probe, preparation and application of the beta-amyloid protein targeting fluorescent probe in Alzheimer's disease. The structural formula of the fluorescent probe is as shown in formula I in the specification. The fluorescent probe disclosed by the invention is a compound taking 6-dimethylamino-1-methylquinoline as a parent structure, and the fluorescent probe has the advantages of long emission wavelength, large Stock shift, capability of specifically detecting beta amyloid protein, sensitivity to viscosity in tissue cells, and good response to the viscosity. After the fluorescent probe is combined with beta amyloid protein in the brain of a patient suffering from the Alzheimer's disease, a fluorescence signal is obviously enhanced, and the fluorescent probe can be used for detecting the beta amyloid protein and early diagnosing the Alzheimer's disease and has important guiding significance on development of diagnosis and treatment probes of the Alzheimer's disease.

Near-infrared fluorescent probe, preparation and application of near-infrared fluorescent probe in detection of transthyroxine tetramer protein

The invention discloses a near-infrared fluorescent probe, preparation and an application of the near-infrared fluorescent probe in detection of transthyroxine tetramer protein. The structural formula of the near-infrared fluorescent probe is shown as a formula (I). The preparation method comprises the following steps: adding 2-aldehyde-6-dimethylaminoquinoline, 2-acetonitrile benzothiazole and tetrabutylammonium bromide into ethanol, carrying out a reflux reaction under the conditions of sealing and oil bath at 80 +/-5 DEG C, cooling to room temperature after the reaction is finished, standing to separate out a solid, carrying out suction filtration, and washing to obtain the near-infrared fluorescent probe. The fluorescent probe prepared in the invention has near-infrared emission wavelength, and can be used for detecting the content of transthyretin tetramer protein and diagnosing transthyretin familial amyloidosis.

A quinoline-benzothiazole hybrid as the first near-infrared fluorescent probe for transthyretin

Transthyretin (TTR) amyloidosis is a disease caused by the misfolding and aggregation of TTR protein, including familial amyloidotic polyneuropathies (FAP), senile systemic amyloidosis (SSA), familial amyloidotic cardiomyopathies (FAC), Alzheimer's disease (AD), etc. Nowadays, the emission wavelength of reported probes for wild-type TTR is relatively short, which restricts their further application. In this study, a quinoline-benzothiazole conjugated scaffold (QCN-2) was rationally designed and synthesized as the first near-infrared fluorescent (NIRF) probe for the determination of TTR content. QCN-2 displayed remarkable turn-on fluorescence (25-fold) with high sensitivity when bound to wild-type TTR (detection limit, 204.4 nM). Moreover, the molecular docking study indicated that the benzothiazole moiety could enter the inner cavity binding site, and the cyano group could form a hydrogen bond with LYS15 residues, which might restrict the rotation of the vinyl bond, leading to increasing the ICT process and emission intensity. All these excellent properties of this probe make it a robust and promising tool for the diagnosis of diseases related to TTR amyloidosis.

Synthesis and efficacy of pyrvinium-inspired analogs against tuberculosis and malaria pathogens

Herein, we report the synthesis and evaluation of pyrvinium-based antimalarial and antitubercular compounds. Pyrvinium is an FDA approved drug for the treatment of pinworm infection, and it has been reported to have antiparasitic and antimicrobial activities. Pyrvinium contains quinoline core coupled with pyrrole. We replaced the pyrrole with various aryl or heteroaryl substituents to generate pyrvinium analogs. The profiling of these compounds against malaria parasite P. falciparum 3D7 revealed analogs with better antimalarial activity than pyrvinium pamoate. Compound 14 and 16 showed IC50 of 23 nM and 60 nM against P. falciparum 3D7, respectively. These compounds were also effective against drug-resistant malaria parasite P. falciparum Dd2 with IC50 of 53 nM and 97 nM, respectively. The cytotoxicity against CHO-K1, HEK and NRK-49F cells revealed better selectivity index for these new analogs compared to pyrvinium. Additionally, this series of compounds showed activity against M. tuberculosis H37Rv; particularly compounds 10, 13, 14 and 16 showed equipotent antitubercular activity to that of pyrvinium pamoate. The compounds 14 and 16 should be taken forward as leads for further optimization.

Human serum protein fluorescent probe as well as preparation method and application thereof

The invention discloses a human serum protein fluorescent probe as well as a preparation method and application thereof. The human serum protein fluorescent probe has a structure shown in the specification. The fluorescent probe disclosed by the invention is capable of rapidly and highly selectively detecting human serum proteins and has potential of preclinical detection. The invention disclosesthe preparation method of the florescent probe, a related activity testing method and related activity data of the florescent probe.

Cyslization derivative fluorescent probe as well as preparation method and application thereof

The invention relates to a cyslization derivative fluorescent probe as well as a preparation method and application thereof. The name of the compound is 2-cyano-3-(6-(dimethylamino)quinoline-2-yl) acrylate. The compound provided by the invention is small in molecular mass, simple in structure and capable of serving as a molecular sensor to sensitively and selectively detect sulfite in living cellsand start a fluorescence reaction. The detection mechanism is not affected by sulfide and a sulfhydryl compound and has the characteristic of high selectivity, what is more outstanding is that. The fluorescent molecular probe almost has no toxicity to cells , has a very good cell membrane permeation effect and is capable of permeating a living cell membrane within 2 min to start the fluorescencereaction. The cyslization derivative fluorescent probe provides a novel method for detecting endogenous sulfite of the living cell so as to have very important practical significance.