4295-36-7

Basic information

• Product Name: 2,3-Dihydro-1H-quinolin-4-one
• Synonyms: 2,3-DIHYDROQUINOLIN-4(1H)-ONE;2,3-DIHYDRO-1H-QUINOLIN-4-ONE;AKOS 93029;4(1H)-QUINOLINONE, 2,3-DIHYDRO-;2,3-DIHYDRO-1H-QUINOLINE-4-ONE;1,2,3,4-tetrahydro-4-quinolinone hydrochloride;1,2,3,4-Tetrahydroquinolin-4-one;2,3-Dihydro-1H-quinolin-4-one HCl
• CAS NO: 4295-36-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 275-428-6
• Product Categories: pharmacetical
• Mol File: 4295-36-7.mol
• Article Data: 35

Chemical Properties

• Melting Point: 44 °C
• Boiling Point: 301 °C at 760 mmHg
• Flash Point: 142.8 °C
• Appearance: /
• Density: 1.142 g/cm³
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 2.68±0.20(Predicted)
• CAS DataBase Reference: 2,3-Dihydro-1H-quinolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydro-1H-quinolin-4-one(4295-36-7)
• EPA Substance Registry System: 2,3-Dihydro-1H-quinolin-4-one(4295-36-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 4295-36-7(Hazardous Substances Data)

Usage

Uses

2,3-Dihydro-1H-quinolin-4-one is a beta-adrenergic blocking agents.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1901, 1949 DOI: 10.1021/ja01174a001

InChI:InChI=1/C9H9NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-4,10H,5-6H2

Synthetic route

1-phenylazetidin-2-one (5099-95-6) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 0 - 18℃; for 1h; Fries rearrangement; Inert atmosphere;	98%
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 0 - 20℃; for 0.25h;	96%
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 0 - 20℃; for 0.25h;	96%

1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-4-quinolinone (179898-00-1) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
In acetonitrile at 300℃; under 75007.5 Torr;	95%

3-(phenylsulfonyl)-2,3-dihydroquinolin-4(1H)-one → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 130℃; for 3h; Inert atmosphere; Sealed tube;	90%

1-tosyl-2,3-dihydroquinolin-4(1H)-one (14278-37-6) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With hydrogenchloride; acetic acid for 3.5h; Heating;	83%
With hydrogenchloride; water; acetic acid

1-(2-nitrophenyl)-2-propen-1-one (68165-36-6) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Stage #1: 1-(2-nitrophenyl)prop-2-en-1-one With hydrogenchloride at 80 - 85℃; Inert atmosphere; Stage #2: With iron at 100℃; for 1h; Inert atmosphere;	83%

N-(2-(3-hydroxyprop-1-yn-1-yl)phenyl)-4-methylbenzenesulfonamide (665033-49-8) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With trifluorormethanesulfonic acid; α,α,α-trifluorotoluene for 8h; Meyer-Schuster Rearrangement; Reflux;	82%

N-phenyl-β-alanine (5652-38-0) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With Acide polyphosphorique at 120 - 130℃; for 1h;	70%
With polyphosphoric acid at 50℃; for 3.5h;	49%
Stage #1: N-phenyl-β-alanine With Eaton's reagent at 70℃; Friedel Crafts Acylation; Stage #2: With sodium hydroxide; water at 0℃;	46.3%

ethyl 3-phenylaminopropionate (62750-11-2) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 130℃; for 5h; Inert atmosphere;	68%
Multi-step reaction with 2 steps 1: ethylmagnesium bromide / tetrahydrofuran / 14 h 2: 80 percent / trifluoroacetic acid / 1 h / 100 °C View Scheme

3-(2-aminophenyl)propyn-1-ol → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With tin(ll) chloride In water; tert-butyl alcohol for 1h; Reagent/catalyst; Meyer-Schuster Rearrangement; Reflux; Sealed tube;	66%

1-acetyl-1,2,3,4-tetrahydroquinolin-4-one (64142-63-8) → 6-Acetyl-2,3-dihydro-4(1H)-quinolinone (146943-76-2) + 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With PPA at 120℃; for 0.166667h;	A 11.7% B 51.2%
With PPA In acetonitrile at 120℃; for 0.5h; Mechanism; Irradiation;	A 11.7% B 51.2%

N-[2-(3-hydroxypropyl-1-ynyl)phenyl]-4-benzamide → 2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 1-benzoyl-2,3-dihydro-1H-quinolin-4-one (99293-89-7)

Conditions	Yield
With trifluorormethanesulfonic acid; α,α,α-trifluorotoluene for 6h; Meyer-Schuster Rearrangement; Reflux;	A 25% B 50%

2-(2-(hydroxymethyl)ethynyl)aniline (125812-44-4) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With trifluorormethanesulfonic acid; α,α,α-trifluorotoluene for 6h; Meyer-Schuster Rearrangement; Reflux;	50%
With toluene-4-sulfonic acid In benzene Reflux; Green chemistry;	10%
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 - 20 °C 2: α,α,α-trifluorotoluene; trifluorormethanesulfonic acid / 8 h / Reflux View Scheme

4-chloro-N-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-benzamide → 2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 1-(4-chloro-benzoyl)-2,3-dihydro-1H-quinolin-4-one

Conditions	Yield
With trifluorormethanesulfonic acid; α,α,α-trifluorotoluene for 6h; Meyer-Schuster Rearrangement; Reflux;	A 25% B 40%

4-fluoro-N-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-benzamide → 2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 1-(4-fluoro-benzoyl)-2,3-dihydro-1H-quinolin-4-one

Conditions	Yield
With trifluorormethanesulfonic acid; α,α,α-trifluorotoluene for 6h; Meyer-Schuster Rearrangement; Reflux;	A 25% B 35%

ethyl 1-phenyl-1,4,5,6-tetrahydropyridazine-3-carboxylate (137116-93-9) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With PPA; Polyphosphoric acid (PPA) at 110℃; for 0.25h;	19%

4-oxo-1,2,3,4-tetrahydro-quinoline-3-carboxylic acid methyl ester (1136-75-0) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With hydrogenchloride; water

methyl 3-(o-methoxycarbonylanilino)propionate (38113-64-3) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 4-oxo-1,2,3,4-tetrahydro-quinoline-3-carboxylic acid methyl ester (1136-75-0)

Conditions	Yield
With ethanol; sodium; benzene
With sodium; xylene

1-p-toluenesulfonyl-4-chloro-1.2-dihydro-quinoline → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
With hydrogenchloride; acetic acid

hydrogenchloride (7647-01-0) + N-(p-toluenesulfonyl)-4-chloro-1,2-dihydroquinoline (856089-56-0) + acetic acid (64-19-7) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

aniline (62-53-3) + Wang resin-bound styrene 4 → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 100 °C 2: polyphosphoric acid / 100 °C View Scheme

methyl 3-(phenylamino)propanoate (21911-84-2) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 0.33 h / Heating 2: aq. HCl / dioxane / 3 h / Heating 3: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 4: 83 percent / gl. AcOH, aq. HCl / 3.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: pyridine 2: aqueous methanol. KOH-solution 3: phosphorus (V)-chloride; benzene / Behandeln des erhaltenen Reaktionsgemisches mit Zinn(IV)-chlorid in Benzol. 4: acetic acid; water; hydrochloric acid View Scheme

methyl 3-[N-phenyl-N-(p-toluenesulfonyl)amino]propionate (17266-98-7) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. HCl / dioxane / 3 h / Heating 2: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 3: 83 percent / gl. AcOH, aq. HCl / 3.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: aqueous methanol. KOH-solution 2: phosphorus (V)-chloride; benzene / Behandeln des erhaltenen Reaktionsgemisches mit Zinn(IV)-chlorid in Benzol. 3: acetic acid; water; hydrochloric acid View Scheme

N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine (65148-06-3) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 2: 83 percent / gl. AcOH, aq. HCl / 3.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: phosphorus (V)-chloride; benzene / Behandeln des erhaltenen Reaktionsgemisches mit Zinn(IV)-chlorid in Benzol. 2: acetic acid; water; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: xylene; phosphorus (V)-oxide / 138 °C 2: acetic acid; water; hydrochloric acid View Scheme
Stage #1: N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine With oxalyl dichloride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: With aluminum (III) chloride at 0 - 20℃; for 2h; Inert atmosphere;	9.8 g

aniline (62-53-3) + p-toluenesulfonic acid--ester → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: AcOH / 22 h / Heating 2: pyridine / 0.33 h / Heating 3: aq. HCl / dioxane / 3 h / Heating 4: 1.) PCl5, 2.) AlCl3 / 1.) benzene, from 5 deg C to 23 deg C, 30 min, 2.) benzene 15-20 deg C, 3.5 h 5: 83 percent / gl. AcOH, aq. HCl / 3.5 h / Heating View Scheme

aniline (62-53-3) + 2-halogen-aniline → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: conc. hydrochloric acid / ethanol / 48 h / Heating 2: ethylmagnesium bromide / tetrahydrofuran / 14 h 3: 80 percent / trifluoroacetic acid / 1 h / 100 °C View Scheme

ethyl 5-chloro-2-oxopentanoate phenylhydrazone (137116-95-1) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 41 percent / K2CO3 / ethanol / 24 h / Heating 2: 19 percent / polyphosphoric acid (PPA) / 0.25 h / 110 °C View Scheme

aniline (62-53-3) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic acid 2: pyridine 3: aqueous methanol. KOH-solution 4: phosphorus (V)-chloride; benzene / Behandeln des erhaltenen Reaktionsgemisches mit Zinn(IV)-chlorid in Benzol. 5: acetic acid; water; hydrochloric acid View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / dichloromethane / 3 h / 20 °C 2: sodium t-butanolate / N,N-dimethyl-formamide / 2 h / 20 °C 3: trifluorormethanesulfonic acid / 1,2-dichloro-ethane View Scheme
Multi-step reaction with 2 steps 1: acetic acid / methanol / 61 h / 20 °C / Reflux 2: methanesulfonic acid; phosphorus pentoxide / 5 h / 130 °C / Inert atmosphere View Scheme

3-bromo-N-phenylpropanamide (7661-07-6) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate / N,N-dimethyl-formamide / 2 h / 20 °C 2: trifluorormethanesulfonic acid / 1,2-dichloro-ethane View Scheme
Multi-step reaction with 2 steps 1: sodium t-butanolate / N,N-dimethyl-formamide / 3 h / 0 - 20 °C 2: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium t-butanolate / N,N-dimethyl-formamide / 3 h / 20 °C 2: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 2 h / 0 - 20 °C View Scheme

2-nitro-benzaldehyde (552-89-6) → 2,3-dihydroquinolin-4(1H)-one (4295-36-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2.1: Jones reagent / water; acetone / 1 h / 23 °C / Inert atmosphere 3.1: hydrogenchloride / 80 - 85 °C / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere View Scheme

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + di-tert-butyl dicarbonate (24424-99-5) → 1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-4-quinolinone (179898-00-1)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 60℃; for 16h;	100%
Stage #1: 2,3-dihydroquinolin-4(1H)-one; di-tert-butyl dicarbonate In tetrahydrofuran for 16h; Heating / reflux; Stage #2: With sodium hydroxide In water; ethyl acetate	78%
With dmap; triethylamine In dichloromethane at 20℃; for 2h;	74%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) → (R)-1,2,3,4-tetrahydroquinolin-4-ol

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H64FeNOP; hydrogen; sodium t-butanolate In isopropyl alcohol at 25 - 30℃; under 38002.6 Torr; for 12h; Autoclave; enantioselective reaction;	99%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + thiosemicarbazide (79-19-6) → 2,3-dihydro-1H-quinoline-4-one thiosemicarbazone (1431552-20-3)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 36h; Reflux;	97%

2-furancarbonyl chloride (527-69-5) + 2,3-dihydroquinolin-4(1H)-one (4295-36-7) → furan-2-yl(4-hydroxy-3,4-dihydroquinolin-1(2H)-yl)methanone (367509-07-7) + 1-(2-furoyl)-2,3-dihydro-4(1H)-quinolinone (367509-08-8)

Conditions	Yield
	A 95% B n/a

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + benzyl chloroformate (501-53-1) → 1-benzyloxycarbonyl-2,3-dihydro-4-quinolone (934192-22-0)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 0 - 25℃; for 4h;	93%
With potassium carbonate In tetrahydrofuran; water at 0 - 25℃; for 24h;	93%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	83%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate (217813-03-1) → 1-methoxy-10-(3-methoxyphenyl)acridin-9(10H)-one (1385731-29-2)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 24h;	90%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 4-bromomethyltrifluoromethylbenzene (402-49-3) → 1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroquinolin-4-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 1.5h; Microwave irradiation;	87.4%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) → 4(1H)-quinolinone (529-37-3)

Conditions	Yield
With palladium 10% on activated carbon; sodium hydroxide In water; isopropyl alcohol for 16h; Inert atmosphere; Reflux;	87%
With palladium on activated charcoal; water

tetrahydrofuran (109-99-9) + 2,3-dihydroquinolin-4(1H)-one (4295-36-7) + trimethylsilyl cyanide (7677-24-9) → 5-hydroxy-2-(4-oxo-3,4-dihydroquinolin-1(2H)-yl)pentanenitrile

Conditions	Yield
Stage #1: tetrahydrofuran With copper (I) acetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 20℃; for 0.25h; Inert atmosphere; Stage #2: 2,3-dihydroquinolin-4(1H)-one; trimethylsilyl cyanide With ammonium chloride; N-fluorobis(benzenesulfon)imide at 20℃; for 8h; Inert atmosphere;	87%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) → 6-bromo-2,3-dihydro-1H-quinolin-4-one (76228-06-3)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 0℃; for 1.5h;	86%
With N-Bromosuccinimide In dichloromethane at 20℃; for 1.5h;
With N-Bromosuccinimide In dichloromethane at 20℃; for 1.5h;

2,3-dihydroquinolin-4(1H)-one (4295-36-7) → (3,4-dimethoxyphenyl)(4-hydroxy-3,4-dihydroquinolin-1(2H)-yl)methanone (367509-05-5) + 1-(3,4-dimethoxybenzoyl)-2,3-dihydroquinolin-4(1H)-one (367509-06-6)

Conditions	Yield
	A 86% B n/a

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate → 10-(3,4-dimethoxyphenyl)-2,3-dimethoxyacridin-9(10H)-one (1385731-26-9)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 24h;	85%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 2-amino-benzenethiol (137-07-5) → 12H-quino<3,4-b>-1,4-benzothazine (97819-50-6)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 110℃; for 10h;	84%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + trimethylsilyl cyanide (7677-24-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-(4-oxo-3,4-dihydroquinolin-1(2H)-yl)acetonitrile

Conditions	Yield
With copper diacetate; N-fluorobis(benzenesulfon)imide; 4,4'-di-tert-butyl-2,2'-bipyridine at 20℃; for 16h; Inert atmosphere;	81%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 10-phenylacridin-9(10H)-one (5472-23-1)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 24h;	77%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + chlorodifluoroacetic anhydride (2834-23-3) → 1-(2-chloro-2,2-difluoroacetyl)-2,3-dihydroquinolin-4(1H)-one

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	74%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate → 10-(3,4-dimethylphenyl)-2,3-dimethylacridin-9(10H)-one (1385731-25-8)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 24h;	73%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 1-phenyl-2,3-dihydro-1H-quinolin-4-one (10258-13-6) + 10-phenylacridin-9(10H)-one (5472-23-1)

Conditions	Yield
With cesium fluoride In acetonitrile at 23℃; for 2h;	A 20% B 73%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + 6-(trimethylsilyl)-5-indanyl triflate → 10-(3,4-dimethoxyphenyl)-2,3-dimethoxyacridin-9(10H)-[b]acridin-10(5H)-one (1385731-28-1)

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 24h;	69%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + methyl iodide (74-88-4) → 1-methyl-1,2,3,4-tetrahydroquinolin-4-one (1198-15-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	68%
With potassium carbonate In acetone at 80℃; for 16h;	61%
With potassium carbonate In acetone at 80℃; for 16h;	50%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) + acetic anhydride (108-24-7) → 6-nitro-1,2,3,4-tetrahydroquinolin-4-one (57445-29-1) + 1-acetyl-1,2,3,4-tetrahydroquinolin-4-one (64142-63-8) + 1-nitro-2,3-dihydro-1H-quinolin-4-one (1431552-24-7)

Conditions	Yield
With nitric acid; acetic acid at 0 - 20℃;	A 25% B 12% C 65%

Upstream product

• 62750-11-2 ethyl 3-phenylaminopropionate 
• 62-53-3 aniline 
• 65148-06-3 N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine 
• 17266-98-7 methyl 3-[N-phenyl-N-(p-toluenesulfonyl)amino]propionate 
• 21911-84-2 methyl 3-(phenylamino)propanoate 
• 7647-01-0 hydrogenchloride 
• 856089-56-0 N-(p-toluenesulfonyl)-4-chloro-1,2-dihydroquinoline 
• 64-19-7 acetic acid 
• 137116-93-9 ethyl 1-phenyl-1,4,5,6-tetrahydropyridazine-3-carboxylate 
• 5652-38-0 N-phenyl-β-alanine 
• 64142-63-8 1-acetyl-1,2,3,4-tetrahydroquinolin-4-one 
• 5099-95-6 1-phenylazetidin-2-one 
• 14278-37-6 1-tosyl-2,3-dihydroquinolin-4(1H)-one 
• 38113-64-3 methyl 3-(o-methoxycarbonylanilino)propionate 

Downstream Products

• 179898-00-1 1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-4-quinolinone 
• 611-35-8 4-chloroquinoline 
• 906630-76-0 3-veratryl-quinolin-4-ol 

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Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as preparation method and application thereof

The invention discloses 2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as a preparation method and application thereof. The structural formula of the derivatives is as shown in a formula (I): (the formula is as shown in the description), wherein R1 is halogen, alkyl or alkoxy; R2 is hydrogen, halogen or alkoxy; R3 is hydrogen or halogen; R4 is hydrogen or halogen; X is hydrogen, acetyl or nitryl; and Y is hydrogen or phenyl. The derivatives can obviously inhibit proliferation of tumor cells, and has significant inhibition effect on multiple cancer cell strains such asbreast cancer cells, melanoma cells and prostatic cancer cells; and the anti-tumor activity is obviously better than that of a broad-spectrum anti-cancer medicine cis-platinum. In addition, the preparation process of the derivatives is simple, the conditions are mild, the sources of the raw materials are rich, the production cost is low, and potential medicinal value and good application prospectin the aspect of preparing a novel anti-tumor medicine are achieved.

HETEROCYCLIC COMPOUND

The present invention relates to a compound which can be useful for the treatment or prevention of SPT-related diseases including cancer and congenital diseases associated with sphingolipid accumulation (including Niemann-Pick disease).