ChemicalBook CAS DataBase List Indol-1-yl-acetic acid

Indol-1-yl-acetic acid synthesis

12synthesis methods

Product Name:Indol-1-yl-acetic acid
CAS Number:24297-59-4
Molecular formula:C10H9NO2
Molecular Weight:175.18

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24297-59-4

Step 2: Preparation of 2-(1H-indol-1-yl)acetic acid Ethyl 2-(1H-indol-1-yl)acetate (2.03 g, 10 mmol) was dissolved in ethanol (40 mL), aqueous sodium hydroxide solution (1 N, 50 mL) was added, and the reaction was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction solution was adjusted to slightly acidic with dilute hydrochloric acid and the mixture was subsequently concentrated under reduced pressure. The residue was extracted with ethyl acetate and the organic phase was washed with brine and the solvent was removed under reduced pressure to give pure 2-(1H-indol-1-yl)acetic acid (1.6 g, 87% yield), (LC/MS: m/z = 176.3 [M+H]+).

120-72-9 Synthesis

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105-36-2 Synthesis

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Yield: 92%

Reaction Conditions:

with sodium hydroxide;tetrabutylammomium bromide in water;benzene

Steps:

1 (1H-Indol-1-yl)acetic Acid
EXAMPLE 1 (1H-Indol-1-yl)acetic Acid To a solution of ethyl 2-bromoacetate (25 g, 0.15 mole) and indole (11.7 g, 0.1 mole) in 100 ml of benzene is added a solution of sodium hydroxide (25 g, 0.626 mole) in 50 ml of water. To the obtained mixture is added tetra-n-butylammonium bromide (1.6 g, 0.5 mmole). The mixture is stirred at 25° C. for 16 hours. The aqueous phase is acidified to pH 3. The organic phase is separated, dried and evaporated to give the title compound in 92% yield. NMR (DMSO-D₆) ppm (δ) 5.05 (s,2); 6.50 (d, 1), 6.9- 7.8 (m, 5).

References:

Yeda Research and Development Co. Ltd. US4139703, 1979, A

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References