5760-20-3

Basic information

• Product Name: 2-Quinolinemethanamine
• Synonyms: RARECHEM AL BW 2222;AKOS AUF02056;C-QUINOLIN-2-YL-METHYLAMINE;CHEMBRDG-BB 4102058;2-aminomethylquinoline;Quinolin-2-yl-methylamine;2-Quinolinemethanamine;Quinoline-2-methaneamine
• CAS NO: 5760-20-3
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.2
• Mol File: 5760-20-3.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 292.3 °C at 760 mmHg
• Flash Point: 155.6 °C
• Appearance: /
• Density: 1.156 g/cm³
• Vapor Pressure: 0.00185mmHg at 25°C
• Refractive Index: 1.662
• PKA: 8.70±0.30(Predicted)
• CAS DataBase Reference: 2-Quinolinemethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinolinemethanamine(5760-20-3)
• EPA Substance Registry System: 2-Quinolinemethanamine(5760-20-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5760-20-3(Hazardous Substances Data)

Usage

General Description

2-Quinolinemethanamine, also known as N-(quinolin-2-yl)methanamine, is a chemical compound with the molecular formula C10H10N2. It is an aromatic amine that contains a quinoline ring, and is commonly used in pharmaceutical research and as a building block for the synthesis of various organic compounds. 2-Quinolinemethanamine has been studied for its potential use in the treatment of various diseases and medical conditions, and has shown promise in anti-inflammatory and antimicrobial applications. It is also used as a reagent in organic synthesis and can be found in some commercial products. Overall, 2-Quinolinemethanamine is a versatile chemical compound with various potential applications in the fields of medicine and organic chemistry.

InChI:InChI=1/C10H10N2/c11-7-9-6-5-8-3-1-2-4-10(8)12-9/h1-6H,7,11H2

Synthetic route

2-(quinolin-2-ylmethyl)isoindoline-1,3-dione (67868-38-6) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With hydrazine hydrate for 12h; Reflux;	85%
With hydrazine hydrate In ethanol for 5h; Reflux;

1-((quinoline-2-yl)methyl)pyrrolidine-2,5-dione → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With hydrazine hydrate for 12h; Reflux;	85%

quinolin-2-ylmethanamine bischlorohydrate (18004-62-1) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With sodium hydroxide In water pH=10;	82%

quinoline-2-carbonitrile (1436-43-7) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal	76%
With palladium 10% on activated carbon; hydrogen In acetic acid at 20℃; under 10343.2 Torr; for 6h; Autoclave;	46%
With hydrogen; trifluoroacetic acid; palladium on activated charcoal In methanol under 1551.4 Torr; for 2h; Ambient temperature;

quinoline-2-carbaldehyde oxime (1131-68-6) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With acetic acid; zinc In ethanol at 20℃; for 13h;	73%
With trifluoroacetic acid; zinc at 20℃;	71%

(E)-2-quinolinecarbaldehyde oxime (126921-73-1) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With ethanol; acetic acid; zinc

quinoline-2-carbonitrile (1436-43-7) + chromium (II)-acetate → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With potassium hydroxide

Quinoline N-oxide (1613-37-2) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / benzoyl chloride 2: 76 percent / hydrogen / Pd/C View Scheme

quinoline-2-carboxylic acid (93-10-7) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: CH2Cl2 / 0.5 h 2: NH3 / CH2Cl2 / 0.05 h 3: 89 percent / triethylamine, trifluoroacetic anhydride / CH2Cl2 / 0.03 h / 0 °C 4: H2, trifluoroacetic acid / 10percent Pd/C / methanol / 2 h / 1551.4 Torr / Ambient temperature View Scheme

quinoline-2-carboxamide (5382-42-3) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / triethylamine, trifluoroacetic anhydride / CH2Cl2 / 0.03 h / 0 °C 2: H2, trifluoroacetic acid / 10percent Pd/C / methanol / 2 h / 1551.4 Torr / Ambient temperature View Scheme

1-imidazolyl-2-quinolinylmethanone (123005-03-8) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: NH3 / CH2Cl2 / 0.05 h 2: 89 percent / triethylamine, trifluoroacetic anhydride / CH2Cl2 / 0.03 h / 0 °C 3: H2, trifluoroacetic acid / 10percent Pd/C / methanol / 2 h / 1551.4 Torr / Ambient temperature View Scheme

quinoline-2-carbonitrile (1436-43-7) + aqueous hydroxide → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
palladium In water; acetic acid

N,N-di-Boc-quinolin-2-ylmethanamine (1393887-11-0) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol / 0 - 90 °C 2: sodium hydroxide / water / pH 10 View Scheme

quinoline-2-carboxylic acid methyl ester (19575-07-6) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 - 35 °C 2: phosphorus tribromide / dichloromethane / 0 - 20 °C 3: potassium carbonate / acetonitrile / 2 h / 20 °C / Reflux 4: hydrogenchloride / ethanol / 0 - 90 °C 5: sodium hydroxide / water / pH 10 View Scheme

quinolin-2-ylmethanol (1780-17-2) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: phosphorus tribromide / dichloromethane / 0 - 20 °C 2: potassium carbonate / acetonitrile / 2 h / 20 °C / Reflux 3: hydrogenchloride / ethanol / 0 - 90 °C 4: sodium hydroxide / water / pH 10 View Scheme
Multi-step reaction with 3 steps 1: phosphorus tribromide; triethylamine / dichloromethane / 20 °C / Cooling with ice 2: sodium azide / N,N-dimethyl-formamide / 20 °C 3: triphenylphosphine / tetrahydrofuran; water / 5 h / 20 °C View Scheme

quinolin-2-ylmethylbromide (5632-15-5) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 2 h / 20 °C / Reflux 2: hydrogenchloride / ethanol / 0 - 90 °C 3: sodium hydroxide / water / pH 10 View Scheme
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 20 °C 2: triphenylphosphine / tetrahydrofuran; water / 5 h / 20 °C View Scheme

quinoline-2-carbaldehyde oxime (1131-68-6) → 2-aminomethylquinoline (5760-20-3) + bis(quinolin-2-ylmethyl)amine

Conditions	Yield
With hydrogen In tetrahydrofuran; methanol at 50℃; under 3102.97 Torr; for 12h;

quinoline 2-carbaldehyde (5470-96-2) → 2-aminomethylquinoline (5760-20-3) + bis(quinolin-2-ylmethyl)amine

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 3 h / Reflux 2: hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 3102.97 Torr View Scheme

2-methylquinoline (91-63-4) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: selenium(IV) oxide / 1,4-dioxane / 1 h / Reflux 2: sodium tetrahydroborate / methanol / 0 - 20 °C / Reflux 3: phosphorus tribromide; triethylamine / dichloromethane / 20 °C / Cooling with ice 4: sodium azide / N,N-dimethyl-formamide / 20 °C 5: triphenylphosphine / tetrahydrofuran; water / 5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine; 2,2'-azobis(isobutyronitrile); potassium carbonate / 1,4-dioxane / 24 h / 120 °C / Inert atmosphere 2: hydrazine hydrate / 12 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; triphenylphosphine; 2,2'-azobis(isobutyronitrile); potassium carbonate / 1,4-dioxane / 24 h / 120 °C / Inert atmosphere 2: hydrazine hydrate / 12 h / Reflux View Scheme

2-(azidomethyl)quinoline (13473-67-1) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; water at 20℃; for 5h; Staudinger Azide Reduction;

quinoline 2-carbaldehyde (5470-96-2) → 2-aminomethylquinoline (5760-20-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / methanol / 0 - 20 °C / Reflux 2: phosphorus tribromide; triethylamine / dichloromethane / 20 °C / Cooling with ice 3: sodium azide / N,N-dimethyl-formamide / 20 °C 4: triphenylphosphine / tetrahydrofuran; water / 5 h / 20 °C View Scheme

2-aminomethylquinoline (5760-20-3) → bis(2-quinolylcarbonyl)diimide (1195501-55-3)

Conditions	Yield
Stage #1: 2-aminomethylquinoline With copper(II) acetate monohydrate In ethanol for 24h; in air; Stage #2: With edetate disodium In chloroform; water	100%

2-aminomethylquinoline (5760-20-3) + 1-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-4-[1,2,4]triazol-1-yl-1H-pyrimidin-2-one (232946-83-7) → 4-N-(quinolin-2-ylmethyl)-2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)cytidine

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 23h;	95%

2-aminomethylquinoline (5760-20-3) + (S)-5-(1-((tert-butoxycarbonyl)amino)ethyl)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-1,3-oxazole-4-carboxylic acid → (S)-tert-butyl (1-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-4-((quinolin-2-ylmethyl)carbamoyl)oxazol-5-yl)ethyl)carbamate

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h;	94%

2-aminomethylquinoline (5760-20-3) + methyl fluorobenzenedithiocarboxylate (5969-47-1) → 1-(4-fluorophenyl)imidazo[1,5-a]quinoline

Conditions	Yield
Stage #1: 2-aminomethylquinoline; methyl fluorobenzenedithiocarboxylate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate at 20℃; for 2.5h;	88%
Stage #1: 2-aminomethylquinoline; methyl fluorobenzenedithiocarboxylate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 1.5h;	88%
With iodine In tetrahydrofuran at 20℃; for 2.5h;	83%

2-aminomethylquinoline (5760-20-3) + N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4) → 4-((quinoline-2-methylene)carbamoyl)piperidin-1-carboxylic acid tert-butyl ester

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h;	88%

2-aminomethylquinoline (5760-20-3) + 6-Chloropurine riboside (2004-06-0) → (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((quinolin-2-ylmethyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

Conditions	Yield
With triethylamine In neat (no solvent) at 210℃; under 12929 Torr; for 0.0166667h; Irradiation;	87%

2-aminomethylquinoline (5760-20-3) + methyl dithiobenzoate (2168-78-7) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 1-phenyl-3-(p-tolylthio)imidazo[1,5-a]quinoline

Conditions	Yield
With iodine In ethanol at 80℃; for 14h;	85%

2-aminomethylquinoline (5760-20-3) + benzoyl chloride (98-88-4) → N-(quinolin-2-ylmethyl)benzamide (93323-37-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	84%

2-aminomethylquinoline (5760-20-3) + methyl dithiobenzoate (2168-78-7) + 4-(trifluoromethyl)benzenesulfonyl hydrazide → C24H15F3N2S

Conditions	Yield
With iodine In ethanol at 80℃; for 14h;	84%

2-aminomethylquinoline (5760-20-3) + anthranilic acid amide (28144-70-9) → 2-(2-quinolinyl)-3-hydroquinazolin-4-one (725254-20-6)

Conditions	Yield
With copper(l) iodide; 1,10-phenanthroline-5,6-dione; toluene-4-sulfonic acid In chlorobenzene at 100℃; under 760.051 Torr; for 24h;	84%
With 4-phenylnaphthalene-1,2-dione; oxygen; trifluoroacetic acid In dimethyl sulfoxide at 100℃; for 24h;	60%

2-aminomethylquinoline (5760-20-3) + 2-nitroacetophenone (614-21-1) → 1-phenylimidazo<1,5-a>quinoline

Conditions	Yield
With phosphoric acid at 160℃; for 2h;	84%

2-aminomethylquinoline (5760-20-3) + nitromethane (75-52-5) → Imidazo<1,5-a>quinoline (234-98-0)

Conditions	Yield
With phosphoric acid at 160℃; for 2h;	83%

2-aminomethylquinoline (5760-20-3) → (E)-2-quinolinecarbaldehyde oxime (126921-73-1)

Conditions	Yield
With Acetaldehyde oxime; 3-methyl-4-oxa-5-azahomoadamantane; oxygen In water at 100℃; for 11h; Green chemistry;	82%

2-aminomethylquinoline (5760-20-3) + methyl dithiobenzoate (2168-78-7) → 1-phenylimidazo<1,5-a>quinoline

Conditions	Yield
Stage #1: 2-aminomethylquinoline; methyl dithiobenzoate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate at 20℃; for 2h;	81%
Stage #1: 2-aminomethylquinoline; methyl dithiobenzoate In tetrahydrofuran at 20℃; for 0.75h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 1.5h;	81%

2-aminomethylquinoline (5760-20-3) + methyl dithiobenzoate (2168-78-7) + 4-methoxybenzenesulfonyl hydrazide (1950-68-1) → 3-((4-methoxyphenyl)thio)-1-phenylimidazo[1,5-a]quinoline

Conditions	Yield
With iodine In ethanol at 80℃; for 14h;	80%

2-aminomethylquinoline (5760-20-3) + 5,7-dichloro-3-iso-propyl-pyrazolo[1,5-a]pyrimidine (771510-32-8) → 5-chloro-3-isopropyl-N-(quinolin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	78%

2-aminomethylquinoline (5760-20-3) + di-tert-butyl dicarbonate (24424-99-5) + 4-trifluoromethylbenzoic acid 3-phenylallyl ester → C24H26N2O2

Conditions	Yield
Stage #1: 2-aminomethylquinoline; 4-trifluoromethylbenzoic acid 3-phenylallyl ester With zinc(II) fluoride; bis(η3-allyl-μ-chloropalladium(II)); 1,3-bis-(diphenylphosphino)propane; C29H19F3O2 In toluene at 0℃; for 2h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate With sodium carbonate In dichloromethane Catalytic behavior; Reagent/catalyst;	75%

2-aminomethylquinoline (5760-20-3) + di-tert-butyl dicarbonate (24424-99-5) + C17H12ClF3O2 → C24H25ClN2O2

Conditions	Yield
Stage #1: 2-aminomethylquinoline; C17H12ClF3O2 With zinc(II) fluoride; bis(η3-allyl-μ-chloropalladium(II)); 1,3-bis-(diphenylphosphino)propane; C29H19F3O2 In toluene at 0℃; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate With sodium carbonate In dichloromethane	70%

2-aminomethylquinoline (5760-20-3) + 2-AMINOBENZENESULFONAMIDE (3306-62-5) → 3-(quinolin-2-yl)-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxide (1448256-19-6)

Conditions	Yield
With copper(l) iodide; 1,10-phenanthroline-5,6-dione; toluene-4-sulfonic acid In chlorobenzene at 100℃; under 760.051 Torr; for 24h;	68%

3-formylisoquinoline (5470-80-4) + 2-aminomethylquinoline (5760-20-3) → tris(3-isoquinolylmethyl)amine (189204-41-9)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Schlenk technique;	65%

2-aminomethylquinoline (5760-20-3) + Nitroethane (79-24-3) → 1-methylimidazo[1,5-a]quinoline

Conditions	Yield
With phosphoric acid at 160℃; for 2h;	61%

2-aminomethylquinoline (5760-20-3) + water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) → [Cu(bis(2-quinolylcarbonyl)diimide)(H2O)(OAc)] (1228348-62-6)

Conditions	Yield
In ethanol ligand added to EtOH soln. of Cu compd. (2:1 molar ratio); crystd. on storage for 1 wk, elem. anal.;	58%

2-aminomethylquinoline (5760-20-3) + 1-nitrobutane (627-05-4) → 1-propylimidazo[1,5-a]quinoline (1415734-90-5)

Conditions	Yield
With phosphoric acid at 160℃; for 2h;	56%

2-aminomethylquinoline (5760-20-3) + 1-Nitropropane (108-03-2) → 1-ethylimidazo[1,5-a]quinoline

Conditions	Yield
With phosphoric acid at 160℃; for 2h;	46%

Upstream product

• 1436-43-7 quinoline-2-carbonitrile 
• 126921-73-1 (E)-2-quinolinecarbaldehyde oxime 
• 1613-37-2 Quinoline N-oxide 
• 93-10-7 quinoline-2-carboxylic acid 
• 5382-42-3 quinoline-2-carboxamide 
• 123005-03-8 1-imidazolyl-2-quinolinylmethanone 
• 1131-68-6 quinoline-2-carbaldehyde oxime 
• 67868-38-6 2-(quinolin-2-ylmethyl)isoindoline-1,3-dione 
• 1393887-11-0 N,N-di-Boc-quinolin-2-ylmethanamine 
• 18004-62-1 quinolin-2-ylmethanamine bischlorohydrate 
• 19575-07-6 quinoline-2-carboxylic acid methyl ester 
• 1780-17-2 quinolin-2-ylmethanol 
• 5632-15-5 quinolin-2-ylmethylbromide 
• 5470-96-2 quinoline 2-carbaldehyde 

Downstream Products

• 161315-29-3 ethyl 2-[[4-methoxybenzenesulfonyl]-(2-quinolinylmethyl)amino]acetate 
• 1422360-63-1 C₂₁H₁₉N₅O₂ 
• 93323-37-6 N-(quinolin-2-ylmethyl)benzamide 
• 1544696-09-4 C₂₆H₃₆N₂O₃Si 
• 725254-20-6 2-(2-quinolinyl)-3-hydroquinazolin-4-one 

Relevant articles and documents

Preparation method of N-(aryl/heteroaryl) alkyl-diamide

The invention relates to a preparation method of N-(aryl/heteroaryl)alkyl- diamide, which comprises the following steps: under the protection of nitrogen, sequentially adding transition metal, phosphine or nitrogen ligand, cocatalyst, alkali, solvent, Nhalogenated cyclodiamide, alkyl aromatic ring or alkyl heteroaromatic ring compound into a reaction container, carrying out oxidative amination reaction at 80-140 DEG C, and till the reaction concludes after 6-48 hours, evaporating and drying a solvent and carrying out column chromatography separation to obtain an N (aryl/heteroaryl) alkyl diamide compound. The invention is simple in synthesis process, mild in reaction condition, high in yield and easy to industrialize.

PROCESS FOR PRODUCING OPTICALLY ACTIVE SECONDARY ALCOHOL

[Object] The object of this invention is to provide a method for producing an optically active secondary alcohol at a high optical purity by hydrogenating a substrate carbonyl compound at a high efficiency using as a catalyst a ruthenium complex bearing as a ligand certain optically active diphosphine compound and a readily synthesized amine compound. [Solution] The method of producing an optically active secondary alcohol according to the present invention is characterized in that a substrate carbonyl compound (provided that 3-quinuclidinone, 3-quinuclidinone derivative having a substituent, and a ketone having an aromatic hydrocarbon group and a heterocycle are excluded) is reacted with hydrogen and/or a hydrogen donating compound in the presence of a ruthenium complex selected from the compounds expressed by following general formula (1) RuXYAB (1) [in the general formula (1), X and Y are the same or different from each other and denote a hydrogen atom or an anionic group, A denotes an optically active diphosphine expressed by the general formula (2), B denotes an amine compound expressed by following general formula (3)].

Effective conversion of heteroaromatic ketones into primary amines via hydrogenation of intermediate ketoximes

A process to access heteroaromatic primary amines from the corresponding heteroaromatic ketones has been developed. A broad range of previously reported methods to convert ketones to primary amines was examined on heterocyclic ketones without success, including Leuckart-Wallach conditions, borane reductions, and transition-metal-catalyzed hydrogenations. Unique among the catalysts examined, Raney cobalt produced the desired primary heterocyclic amine. Raney cobalt hydrogenation of structurally varied heterocyclic ketoximes was demonstrated to form primary amines in good selectivity under mild conditions, and the products are easily isolated in high yield. Additionally, this is the first report of a systematic evaluation of the capabilities of Raney cobalt as an oxime hydrogenation catalyst.