120004-79-7

Basic information

• Product Name: 3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone
• Synonyms: 3,4-DIHYDRO-7-(4-CHLOROBUTOXY)-2(1H)-QUINOLINONE;7-(4-CHLOROBUTOXY)-3,4-DIHYDRO-2(1H)-QUINOLINONE;7-(4-Chlorobutoxy)-3,4-Dihydro-2(1H)-quinoline;ARP-B-7-(4-HALOBUTOXY)-3,4-DIHYDROCARBOSTYRIL;7-(4-CHLOROBUTOXY)-3,4-DIHYDRO-2(1H)-QUINOLONE;7-(4-CHLOROBUTOXY)-3,4-DIHYDRO2(1H)-QUINOLINONE:99+%;7-(4-CHLOROBUTOXY)-3,4-DIHYDROC2(1H)-QUINOLINONE;7-(4-chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-one
• CAS NO: 120004-79-7
• Molecular Formula: C₁₃H₁₆ClNO₂
• Molecular Weight: 253.72
• Product Categories: INTERMEDIATESOFARIPIPRAZOLE
• Mol File: 120004-79-7.mol

Chemical Properties

• Melting Point: 100-102 °C(Solv: ethanol (64-17-5))
• Boiling Point: 448.925 °C at 760 mmHg
• Flash Point: 225.302 °C
• Appearance: White to off-white crystalline powder
• Density: 1.187 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.41±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone(120004-79-7)
• EPA Substance Registry System: 3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone(120004-79-7)

Safety Data

• Hazardous Substances Data: 120004-79-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone is used as a key intermediate in the synthesis of aripiprazole, an antipsychotic oral drug. 3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone plays a crucial role in the development and production of medications for the treatment of Schizophrenia, a severe mental disorder that affects millions of people worldwide.
Application Reason:
The use of 3,4-Dihydro-7-(4-chlorobutoxy)-2(1H)-quinolinone in the synthesis of aripiprazole is due to its ability to contribute to the formation of the drug's active pharmaceutical ingredient (API). As an intermediate, it undergoes chemical reactions to form the final drug product, which is then used to manage and treat Schizophrenia in patients.

InChI:InChI=1/C13H16ClNO2/c14-7-1-2-8-17-11-5-3-10-4-6-13(16)15-12(10)9-11/h3,5,9H,1-2,4,6-8H2,(H,15,16)

Upstream product

• 6940-78-9 4-chlorobutyl bromide 
• 22246-18-0 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone 
• 110-56-5 1,4-dichlorobutane 

Downstream Products

• 72723-16-1 deschloro-aripiprazole 
• 173456-48-9 7-{4-[4-(4-Benzyloxy-2,3-dichloro-phenyl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 129722-12-9 aripiprazole 
• 882880-12-8 7-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-oxy)butoxy)-3,4-dihydroquinoline-2(1H)-one 
• 913613-82-8 7-(4-chlorobutoxy)quinoline-2(1H)-one 
• 913611-97-9 Brexpiprazole 

Relevant articles and documents

Industry-Oriented Route Evaluation and Process Optimization for the Preparation of Brexpiprazole

Efforts toward route evaluation and process optimization for the preparation of brexpiprazole (1) are described. Starting from commercially available dihydroquinolinone 11, a three-step synthesis route composed of O-alkylation, oxidation, and N-alkylation was selected for industry-oriented process development aiming to reduce side reactions and achieve better impurity profiles. The reaction conditions of the three steps were investigated, and the control strategy for the process-related impurities was established. The optimized process was validated on the kilogram scale and now is viable for commercialization, with the results of not less than 99.90% purity of 1 (by HPLC) and not more than 0.05% of persistent impurities 15 and 16.

Modular C-H Functionalization Cascade of Aryl Iodides

We report the first example of ipso-borylation for the modular 1,2-bisfunctionalization of aryl iodides via C-H functionalization. The carbon-boron bond is used as a lynchpin to access ipso carbon-carbon, carbon-nitrogen, carbon-oxygen, and carbon-halogen (Cl, Br, I) bonds. The utility of our methodology is illustrated through quick, modular syntheses of the pharmaceuticals Abilify and Flunixin.

Method for preparing

The invention relates to a preparation method of brexpiprazole and an intermediate thereof; the method includes the steps of carrying out a reaction of a compound represented by the formula II with 1-bromo-4-chlorobutane in a reaction solvent to obtain a compound represented by the formula III, in the presence of 2,3-dicyano-5,6-dichlorobenzoquinone, oxidizing the compound represented by the formula III into a compound represented by the formula IV, carrying out a reaction of the compound represented by the formula IV with a compound represented by the formula V to obtain brexpiprazole, then carrying out hydrochloride formation and refining, adding an alkali, and allowing brexpiprazole to drift away. The purity of brexpiprazole obtained by the method is more than 99.5%, the total yield is more than 80%, the process is simple and the cost is low.

Synthetic method of medical intermediate for preparing psychotropic drugs

The invention discloses a synthesis method of a medical intermediate for preparing psychotropic drugs, which comprises the following steps: mixing 1-chloro-4-bromobutane with calcium carbonate and dimethylformamide to obtain the reaction solution A, and mixing 7-hydroxy-3,4-dihydroquinolinone with dimethylformamide to obtain the reaction solution B, mixing the reaction solution A and the reactionsolution B at a temperature of 30 -40 DEG C, and continuing to stir, performing reacting for 4-5 hours, and after detecting, quickly cooling the reactant, performing filtering, and recrystallizing theobtained filter cake with ethanol to obtain the medical intermediate. The synthesis method disclosed by the invention is simple and feasible, the reaction conditions are mild, and the obtained medical intermediate can be used for preparing psychotropic drugs, such as aripiprazole tablets.

A benzothiophene compound of preparation method (by machine translation)

The invention belongs to the field of pharmaceutical chemistry, in particular to a benzothiophene compound preparation method. The present invention has offered a kind of benzo thiophene structure I of the compound of preparation method, route is short, high yield, the operation is simple. Compound II as intermediate for preparing compound I, II by the compound as the starting material for preparing a compound I, high yield, high purity, it is suitable for industrial production. (by machine translation)

Process for preparing aripiprazole

The invention provides a preparation method of aripiprazole shown in the formula (I). The method comprises the following steps of: 1) enabling 7-hydroxy-3,4-dihydro-2(1H) quinolinone shown in the formula (II) to react with a compound represented by the formula (III) in a mixed solvent formed by amide and/or a sulfoxide solvent and water in the presence of an inorganic alkaline compound, thereby preparing a quinolinone compound shown in the formula (IV); and 2) enabling the quinolinone compound represented by the formula (IV) to react with a piperazine compound represented by the formula (V) and/or a salt thereof in the mixed solvent formed by the amide and/or the sulfoxide solvent and the water in the presence of the inorganic alkaline compound, thereby preparing the aripiprazole, wherein a product obtained by the step 1) can be separated from the reaction system or is not separated from the reaction system.

Aralkylpiperidine (or piperazinecarboxylic) and its derivatives used for treating hypercalcemia schinzopherenia

PROBLEM TO BE SOLVED: To provide an agent for treating schizophrenia and related neuropsychiatric diseases.SOLUTION: This invention provides an aralkylpiperidine (or piperazine) derivative represented by formula (1), where A ring is a 5-7 membered heterocycle including N, with the heterocycle including a hetero atom arbitrarily selected from O, S, N; X is O, an amino group or a substituted amino group; Z is CH, N or C; Y is O, N or S; n is an integer of 1-5; and R1-R6 are H, a C1-C4 alkyl group or the like.

PROCESS FOR THE PREPARATION OF ARIPIPRAZOLE

The present invention relates to an improved process for the preparation of high pure crystalline Aripiprazole of formula (I) having low residue ethanol content. The process comprises slurrying Aripiprazole obtained from the reaction mixture with water.

ARALKYL SUBSTITUTED PIPERIDINE OR PIPERAZINE DERIVATIVES AND THEIR USE FOR TREATING SCHIZOPHRENIA

The present invention discloses an aralkyl substituted piperidine or piperazine derivative and the use of the derivative in preparation of medicaments for treating schizophrenia and correlative psychoneuroses. It is shown by pharmacological tests that the derivative of the present invention has better antischizophrenic effect and less toxicity. Said derivative is a free base or salt of the compound having the following general formula.

A NOVEL PROCESS FOR PREPARATION OF ARIPIPRAZOLE AND ITS INTERMEDIATES

A process for the preparation of 7-hydroxy-3,4-dihydro carbostyril (II) by intramolecular Fridel-Craft alkylation of N-(3-methoxyphenyl)-3-chloropropionamide (I) in which an equivalent of N-(3-methoxyphenyl)-3-chloropropionamide (I) is contacted with a Lewis acid (e.g. aluminium chloride) in dimethyl acetamide (DMA), at an elevated temperature of from about 120°C to about 160°C, is provided. The process produces 7-hydroxy-3,4- dihydro carbostyril (II) in high yield and a high state of purity such that it may be used in subsequent .reaction towards the preparation of aripiprazole (IV). Thus 7-hydroxy-3,4- dihydro carbostyril (II) was treated with l-bromo-4-chlorobutane under phase transfer catalyst (PTC) conditions using solvents like acetone or n-butanol at temperature ranging 25°C to 45°C to afford 7-(4-chlorobutoxy)-3,4-dihydro carbostyril (III). The PTC conditions described in this patent afford 7-(4-chlorobutoxy)-3,4-dihydro carbostyril (III) in high purity and high yield with the corresponding dimmer formation is considerably low as compared with the other literature methods of preparing 7-(4-chlorobutoxy)-3,4- dihydro carbostyril (III). Compound (III) was treated with l-(2,3-dichlorophenyl)piperazine, at temperature ranging from 50°C to 100°C, and sodium iodide, potassium carbonate, dimethyl formamide (DMF) as a solvent to afford aripiprazole in high purity and high yield.