Ethyl 1H-indole-3-acetate

white crystalline powder

Ethyl 3-indoleacetate is a member of indole-3-acetic acids.

Ethyl 1H-indol-3-ylacetate Indol-3-ylacetic acid (1.00 g, 5.71 mmol) was dissolved in 25 ml ethanol and concentrated sulphuric acid (1.0 ml, 18.4 mmol) was added. The mixture was stirred at reflux for 2 h and cooled to 0 ºC in an ice bath before neutralization with 2N sodium hydroxide solution. The organics were evaporated under reduced pressure and the mixture was partitioned between dichloromethane and water. The aqueous phase was extracted twice with dichloromethane and the combined organic were washed with brine, dried over sodium sulphate, filtered and evaporated under reduced pressure to give 1.02 g (5.02 mmol, 88percent) of the title compound as a brown oil. Purity 100percent.lndol-3-ylacetic acid (1 .00 g, 5.71 mmol) was dissolved in 25 ml ethanol and concentrated sulphuric acid (1 .0 ml, 18.4 mmol) was added. The mixture was stirred at reflux for 2 h and cooled to 0 °C in an ice bath before neutralization with 2N sodium hydroxide solution. The organics were evaporated under reduced pressure and the mixture was partitioned between dichloromethane and water. The aqueous phase was extracted twice with dichloromethane and the combined organic were washed with brine, dried over sodium sulphate, filtered and evaporated under reduced pressure to give 1 .02 g (5.02 mmol, 88percent) of the title compound as a brown oil. Purity 100percent. To the solution of indole-3-acetic acid (1) (0.01 mol) in absolute ethyl alcohol (25 mL), conc. HGeneral procedure: Indol-3-acetic acid or 2-pyrazine carboxylic acid (5.5 mmol) were heated under reflux for 3 h in 90 mL ethanol and 15 mL concentrated H2SO4. The solution was neutralized with saturated Na2CO3 solution and filtered. The volume was reduced in vacuum and extracted with four 30 mL aliquots of dichloromethane. The combined fractions were washed with 10 mL of water and dried over anhydrous MgSO4. The dichloromethane was removed using vacuum to yield the ethyl carboxylate derivatives, 8a mp. 1–2 °C(Lit. 1–2 °C, Vlaovic et al., 1990) or 8b mp. 46–47 °C (Lit. 48–49 °C, Yoshino et al., 2006) which crystallized on cooling.REFERENCE

Reactant for preparation of:• ;Pesticides1• ;Anti-inflammatory agents2• ;Antibacterial and antifungal agents• ;Anticonvulsant agents • ;Hypotensive agents3• ;Analgesic agents4

Molecular Weight:203.24
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:203.094628657
Monoisotopic Mass:203.094628657
Topological Polar Surface Area:42.1
Heavy Atom Count:15
Complexity:230
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes