ChemicalBook CAS DataBase List 2-METHYLINDOLE-3-ACETIC ACID

2-METHYLINDOLE-3-ACETIC ACID synthesis

13synthesis methods

Product Name:2-METHYLINDOLE-3-ACETIC ACID
CAS Number:1912-43-2
Molecular formula:C11H11NO2
Molecular Weight:189.21

123-76-2 Synthesis

123-76-2
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$5.00/25g

100-63-0 Synthesis

100-63-0
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$10.00/1g

1912-43-2
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$10.00/1g

Yield: 78%

Reaction Conditions:

with acetic acid for 4 h;Reflux;

Steps:

Preparation of compound 2
General procedure: Compound 1 (10 mmol) was dissolved in acetic acid (30 mL), andlevulinic acid (15 mmol) was added to the stirred solution which wasthen refluxed for 4 h. After cooling to room temperature, the mixturewas poured into water (200 mL) and then the solution was treated with30% sodium hydroxide to slight acidity (pH = 5-6). The precipitatedsolid was filtered off, recrystallised from ethanol and dried in vacuo togive compound 2.2-Methylindole-3-acetic acid (2a): Yellow solid, yield 78%, m.p.200-203 °C (199-200 °C14); 1H NMR (500 MHz, CDCl3), δ 2.31 (3H,s, CH3), 3.65 (2H, s, CH2), 6.97 (1H, t, J = 7.5 Hz, ArH), 7.12 (1H, t,J = 7.5 Hz, ArH), 7.23 (1H, d, J = 6.0 Hz, ArH), 7.33 (1H, d, J =6.0 Hz,ArH), 10.83 (1H, s, COOH), 12.15 (1H, s, NH); IR (νmax cm-1): 1504,1518, 1565, 1624, 1769, 2935, 3001, 3535; HRMS m/z 190.0824(calcd 190.0823 for C11H11NO2 [M + H]+)

References:

Wang, Xinying;Liu, Yizhou;Xu, Juan;Jiang, Fanwei;Kang, Congmin [Journal of Chemical Research,2016,vol. 40,# 10,p. 588 - 590]