ChemicalBook CAS DataBase List 2-Methyl-4-nitroindole

2-Methyl-4-nitroindole synthesis

6synthesis methods

Product Name:2-Methyl-4-nitroindole
CAS Number:3484-10-4
Molecular formula:C9H8N2O2
Molecular Weight:176.17

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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95-92-1 Synthesis

95-92-1
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3484-10-4
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Yield: 25% ， 10%

Reaction Conditions:

with potassium ethoxide in dimethyl sulfoxide;N,N-dimethyl-formamide at 0; for 72 h;Reflux;

Steps:

2.2. 2-Methyl-4-nitroindole (4¹⁰)
Without further purification, the imidate ester 3 was used in the reaction: in a 100 mL flask, 3.2 g (14.4 mmol) imidate ester in 12.0 mL anhydrous DMSO were treated with 3.0 mL diethyl oxalate (21.7 mmol, d = 1.076) in 8 mL anhydrous DMF and 1.58 g (18.8 mmol) potassium ethoxide at 0 °C. After 72 h at refluxing, the cooled red reaction mixture was poured onto ice/water and the nitro-indole separated as a red amorphous solid, which was collected and dried under vacuum at 30 °C. Subsequently it was purified by flash chromatography (ethyl acetate/n-hexane 1:1). Yield 25%; mp 192-94 °C; rf 0.63 (ethyl acetate/n-hexane 1:1); ¹H NMR (DMSO-d₆) δ 2.48 (s, 3H, CH₃), 6.79 (d, 1H, J_3,7 = 0.76, 3-H), 7.18 (dd, 1H, J_6,7 = 8.01 Hz, J_6,5 = 8.01 Hz, 6-H), 7.74 (dd, 1H, J_7,6 = 8.01 Hz, J_7,5 = 0.76 Hz, 7-H), 7.98 (dd, 1H, J_5,6 = 8.01 Hz, J_5,7 = 0.76 Hz, 5-H), 11.98 (br s, 1H, NH).

References:

Ferlin, Maria Grazia;Conconi, Maria Teresa;Urbani, Luca;Oselladore, Barbara;Guidolin, Diego;Di Liddo, Rosa;Parnigotto, Pier Paolo [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 1,p. 448 - 457] Location in patent:supporting information; experimental part