ChemicalBook CAS DataBase List 5-HYDROXY-2-METHYL-1-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID ETHYL ESTER

5-HYDROXY-2-METHYL-1-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID ETHYL ESTER synthesis

8synthesis methods

Product Name:5-HYDROXY-2-METHYL-1-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID ETHYL ESTER
CAS Number:5564-29-4
Molecular formula:C18H17NO3
Molecular Weight:295.33

141-97-9 Synthesis

141-97-9
830 suppliers
$5.00/25g

62-53-3 Synthesis

62-53-3
692 suppliers
$10.00/1g

106-51-4 Synthesis

106-51-4
494 suppliers
$10.00/5g

5-HYDROXY-2-METHYL-1-PHENYL-1H-INDOLE-3-CARBOXYLIC ACID ETHYL ESTER

5564-29-4
10 suppliers
$467.00/1g

Yield:5564-29-4 96%

Reaction Conditions:

Stage #1: ethyl 3-oxobutanoate;anilinewith montmorillonite KSF clay in 1,2-dichloro-ethane; for 0.25 h;Reflux;Green chemistry;Nenitzescu Synthesis;
Stage #2: p-benzoquinone in 1,2-dichloro-ethane; for 1 h;Reflux;Green chemistry;Nenitzescu Synthesis;

Steps:

Representative Procedure for the Synthesis of 5-Hydroxyindole Derivatives.

General procedure: A mixture of aniline (1 mmol),dimedone (1 mmol) and montmorillonite KSF clay (0.5 g) in1,2-dichloroethane (5 mL) was kept under reflux for 15 min. To this mixture,1,4-benzoquinone (1 mmol) was added and the resulting mixture was allowed to stir under reflux for the appropriate time (Table 1). After completion of the reaction as indicated by TLC, the mixture was filtered and washed with dichloromethane (10 mL). The combined organic layers were concentrated in vacuo and the resulting residue was purified by column chromatography on silica gel (Merck, 60-120 mesh, ethyl acetate-hexane,1:9) to afford the pure 5-hydroxyindole derivative.

References:

Reddy, B.V.Subba;Reddy, P. Sivaramakrishna;Reddy, Y. Jayasudhan;Bhaskar;Reddy, B. Chandra Obula [Bulletin of the Korean Chemical Society,2013,vol. 34,# 10,p. 2968 - 2972]

591-50-4 Synthesis