Indole-3-acetamide

White powder

Solid

Indole-3-acetamide is a member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA). It has a role as a fungal metabolite, a bacterial metabolite and a plant metabolite. It is a N-acylammonia, a monocarboxylic acid amide and a member of indoles. It derives from an acetamide.

General procedure: The reaction was carried out in a 100-mL stainless steel autoclave. Phenylcyanide (0.10 g, 1.00 mmol) was added to a mixture of ethylenediamine (0.12 g, 2.00 mmol), CoCl26H2O (0.24 g, 1.00 mmol) and Zn (0.07 g, 1.00 mmol) and the vessel was placed in an autoclave. For some of the reactions that were carried out in solvent, 5 mL of solvent was also added. The autoclave was pressurized to 5.00 atm with O2. The mixture was stirred in a preheated oil bath at 120 C for 12 h. Then, the reaction mixture was cooled to room temperature and the product was purified by column chromatography on silica gel using n-hexane:CH2Cl2 (1:1) to give the benzamide(88 percent yield).To a solution of indole—3-acetic acid (1.00 g, 5.70 mmcl, 1.00 equiv.) in THF (15.0 mL, 0.380 M) was added carbonyl diimidazole (1.02 g, 6.28 mmcl, 1 . 10 equiv.) . The resulting solution was stirred at room temperature for 1.5 h. Then NH3 H30 (20.0 mL) was added, and the reaction was stirred at room temperature for 18 h. The solvent wasremoved under reduced pressure, and the residue was purified by column chromatography using EtOAc:hexane (2:1 (v/v)). The purification gave the title compound as a white solid (0.902 g, 5.12 mmcl, 91percent yield). NMR Spectroscopy: 1H NMR (500 MHz, (CD:)3S0, 25 °C, 5): 10.84 (s, 1H), 7.54 (d, IT 7.9 Hz, 1H), 7.33 (d, IT = 8.1 Hz, 1H), 7.26 (s, 1H), 7.17(d, IT = 2.3 Hz, 1H) , 7.06—7.03 (m, 1H), 6.97—6.94 (m, 1.H), 6.80 (s, 1H), 3.45 (s, 2H) . 130 NMR (125 MHz, (CD:hSO, 25 °C, 5): 172.8, 136.0, 127.2, 123.7, 120.8, 118.6, 118.2, 111.2, 109.0, 32.4. All theanalytical data were in good agreement with values reported in the literature (Mauger, J. et al. 1989).General procedure: The mixtures of IAA (175mg, 1mmol), HOBT (153mg, 1mmol), EDCI (170mg, 1.1mmol), DIEA (260μL, 1.5mmol), and the corresponding amines (1.5mmol) in 5mL dichloromethane were stirred at room temperature for 12h. The reaction solvent was removed under reduced pressure, and the obtained residues were purified on silica gel columns eluted with CH

Molecular Weight:174.20
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:174.079312947
Monoisotopic Mass:174.079312947
Topological Polar Surface Area:58.9
Heavy Atom Count:13
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes