3,4-Dihydro-7-hydroxy-2(1H)-quinolinone

Base Information

• Chemical Name: 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone
• CAS No.: 22246-18-0
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.176
• Hs Code.: 29334900
• UNII: VFU6XCR3Q3
• DSSTox Substance ID: DTXSID70382941
• Nikkaji Number: J28.258H
• Wikidata: Q72465253
• ChEMBL ID: CHEMBL2430711
• Mol file: 22246-18-0.mol

Synonyms:22246-18-0;3,4-Dihydro-7-hydroxy-2(1H)-quinolinone;7-hydroxy-3,4-dihydroquinolin-2(1H)-one;7-Hydroxy-3,4-dihydro-2(1H)-quinolinone;7-hydroxy-3,4-dihydro-1H-quinolin-2-one;3,4-Dihydro-7-hydroxycarbostyril;7-Hydroxy-3,4-dihydrocarbostyril;7-Hydroxy-3,4-dihydro-quinolin-2-one;3,4-dihydroquinoline-2,7-diol;2(1H)-QUINOLINONE, 3,4-DIHYDRO-7-HYDROXY-;VFU6XCR3Q3;CHEMBL2430711;7-hydroxy-1,2,3,4-tetrahydroquinolin-2-one;MFCD06410891;3,4-Dihydro-7-hydroxy-2(1H)-quinoline;3,4-Dihydro-7-hydroxyquinoline-2(1H)-one;7-Oxidanyl-3,4-Dihydro-1~{h}-Quinolin-2-One;7-Hydroxy-3,4-dihydro carbostyril;UNII-VFU6XCR3Q3;Aripiprazole EP Impurity A;SCHEMBL8751;Aripiprazole impurity A [EP];DTXSID70382941;LKLSFDWYIBUGNT-UHFFFAOYSA-N;7-hydroxy-3,4-dihydro-carbostyril;BCP27862;BBL011056;BDBM50493470;s4767;STK617335;STK802230;AKOS005551353;AKOS005622540;AB25068;AC-7028;CCG-266302;CS-W010846;FD18013;GF-0122;HY-W010130;PD088384;SY009657;7-hydroxy-3,4-dihydro-1H-quinoline-2-one;7-hydroxy-3,4-dihydro-2(1H)-quinolineone;7-hydroxy-3,4-dihydro-quinolin-2(1H)-one;AM20060553;ARIPIPRAZOLE IMPURITY A [EP IMPURITY];D3599;FT-0601230;1,2,3,4-Tetrahydroquinoline -7 -ol-2-one;7-(hydroxyl)-3,4-dihydroquinolin-2(1h)-one;7-hydroxy-1,2,3,4-tetrahydroquinoline-2-one;7-Hydroxy-2-oxo-1,2,3,4-tetrahydroquinoline;EN300-155560;3,4-DIHYDRO-7-HYDROXYQUINOLIN-2(1H)-ONE;7-Hydroxy-3,4-dihydro-2(1H)-quinolinone, 97%;A816050;J-511190;Z1255450792;7-Hydroxy-3,4-dihydroquinolin-2(1H)-one;8HJ;Aripiprazole Dihydro Quinolinone Impurity (USP);7-Hydroxycarbostyril

Chemical Property of 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone

Chemical Property:

• Appearance/Colour: Pale yellow powder
• Vapor Pressure: 4.28E-07mmHg at 25°C
• Melting Point: 233-237 °C
• Refractive Index: 1.604
• Boiling Point: 403.7 °C at 760 mmHg
• PKA: 9.60±0.20(Predicted)
• Flash Point: 198 °C
• PSA: 49.33000
• Density: 1.282 g/cm³
• LogP: 1.41490
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99%min. ^*data from raw suppliers

3,4-Dihydro-7-hydroxyquinoline-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC2=C1C=CC(=C2)O
• Description: 3,4-Dihydro-7-hydroxy-2 (1H)-quinolinone is a useful organic and pharmaceutical intermediate. It can be used as the precursor of aripiprazole1, which is an antipsychotic medication. It is also an antitumor agent and hydroxyindole analog inhibitor tyrosinase melanoma.
• Uses: 3,4-Dihydro-7-hydroxyquinoline-2(1H)-one (Aripiprazole EP Impurity A) is an antitumor agent. Hydroxyindole analog inhibitor tyrosinase melanoma. This compound is also used in the preparation of aripiprazole (A771000).

Technology Process of 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone

There total 17 articles about 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

3-chloro-N-(3-hydroxyphenyl)propanamide (50297-40-0) → 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone (22246-18-0)

Guidance literature:

With aluminum (III) chloride; In N,N-dimethyl-formamide; at 90 - 150 ℃; for 6h; Cooling with ice;

Reference yield: 82.0%

N-(3-methoxyphenyl)-3-chloropropionamide (21261-76-7) → 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone (22246-18-0)

Guidance literature:

aluminum (III) chloride; In N,N-dimethyl acetamide; at 140 - 150 ℃; for 2.75h;

Reference yield: 78.0%

C9H7NO5 (1127347-52-7) → 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone (22246-18-0)

Guidance literature:

With ammonium formate on silica gel; zinc; In carbon dioxide; at 50 ℃; under 90009 Torr; Autoclave; liquid CO₂;

DOI:10.3184/030823408X320647

upstream raw materials:

7-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline

3-chloro-N-(3-hydroxyphenyl)propanamide

N-(3-methoxyphenyl)-3-chloropropionamide

m-Anisidine

Downstream raw materials:

7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone

7-(4-chlorobutoxy)-3,4-dihydroquinoline-2(1H)-one

7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl (4-N-oxo)]butoxy}3,4-dihydro-2(1H)-quinolinone

Refernces

• 1、 -. "Preparation method of brexpiprazole intermediate 7-hydroxy-1H-quinoline-2-ketone". Paragraph 0028; 0033-0034. . Retrieved 2021/05/05.
• 2、 Chaturvedi, Radha Nandan,Pendem, Krishnaiah,Patel, Vipul P.,Sharma, Mukta,Malhotra, Sunita. "Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist". . p. 2069 - 2084. Retrieved 2018/08/22.