3-Hydroxyindolin-2-one

Base Information

• Chemical Name: 3-Hydroxyindolin-2-one
• CAS No.: 61-71-2
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 2933790090
• European Community (EC) Number: 826-730-7
• NSC Number: 26319
• DSSTox Substance ID: DTXSID801018937
• Nikkaji Number: J4.817H
• Wikidata: Q27103761
• Metabolomics Workbench ID: 51755
• ChEMBL ID: CHEMBL2152717
• Mol file: 61-71-2.mol

Synonyms:3-hydroxy-2-oxoindole

Chemical Property of 3-Hydroxyindolin-2-one

Chemical Property:

• Vapor Pressure: 4.54E-06mmHg at 25°C
• Boiling Point: 368.2°C at 760 mmHg
• Flash Point: 176.5°C
• PSA: 49.33000
• Density: 1.38g/cm³
• LogP: 0.81010
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

98%min ^*data from raw suppliers

Dioxindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C(=O)N2)O
• Uses: 3-Hydroxy-2,3-dihydro-1H-indol-2-one is a useful reagent for the distereoselective preparation of spiro[furo[3,4-c]chromene-1,3''-indoline]triones.

Technology Process of 3-Hydroxyindolin-2-one

There total 13 articles about 3-Hydroxyindolin-2-one 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: 84.0%

3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one → 3,5-dimethyl-4-nitroisoxazole (1123-49-5) + dioxindol (61-71-2)

Guidance literature:

With sodium tetrahydroborate; In water; at 20 ℃; for 3h;

DOI:10.1039/c9nj03209f

Reference yield: 70.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 2-oxoindole (59-48-3) + dioxindol (61-71-2)

Guidance literature:

indole-2,3-dione; With titanium tetrachloride; zinc; In tetrahydrofuran; at 0 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; water; at 25 ℃; for 0.25h; Temperature; Time;

DOI:10.1016/j.tet.2014.10.071

Reference yield:

indole (120-72-9) → 2-oxoindole (59-48-3) + C16H12N2O4 + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + 2,2-di(3-indolyl)-3-indolone (17646-95-6) + dioxindol (61-71-2)

Guidance literature:

With chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); dihydrogen peroxide; In acetonitrile; at 20 ℃; for 6h; Overall yield = 99 %;

DOI:10.1016/j.apcata.2013.11.023

upstream raw materials:

3,3'-dihydroxy-5-methyl-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione

3,3'-Dihydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione

2,3,4-trioxo-1-methylcarbostyril

dehydroindigo

Downstream raw materials:

3-(2-phenylhydrazono)indolin-2-one

3-hydroxy-1,3-benzopyrimidine-2,4-(1H,3H)-dione

2-oxoindole

indole-2,3-dione

Refernces

Domino Grignard Addition and Oxidation for the One-Pot Synthesis of C2-Quaternary 2-Hydroxyindoxyls

10.1021/acs.orglett.9b03022

The research explores a novel synthetic method to produce a broad range of unnatural C2-quaternary 2-hydroxyindoxyls using a one-pot domino Grignard addition and oxidation process. The purpose of this study is to address the challenge of synthesizing 2-hydroxyindoxyls, which are less explored but significant due to their presence in various natural products and biologically active compounds. The key chemicals involved include 3-hydroxyoxindoles as starting materials and various Grignard reagents such as phenylmagnesium bromide. The reaction proceeds via a 1,2-hydride shift followed by autoxidation, yielding 2-hydroxyindoxyls in high yields. The study concludes that this method offers a simple, scalable, and operationally easy approach to synthesizing a wide range of 2-hydroxyindoxyls with different functional groups. Additionally, the synthesized 2-hydroxyindoxyls can serve as precursors for further transformations, such as the synthesis of bis-indoxyl spirofurans and differentially substituted 3-oxindoles, demonstrating the versatility and potential of this synthetic protocol in organic chemistry.