2-Methyl-5-nitroaniline synthesis

14synthesis methods

Product Name:2-Methyl-5-nitroaniline
CAS Number:99-55-8
Molecular formula:C7H8N2O2
Molecular Weight:152.15

2-Methyl-5-nitrobenzenamine?in concentrated sulfuric acid nitration.

95-53-4 Synthesis

95-53-4
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99-55-8
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Yield:99-55-8 90%

Reaction Conditions:

with sulfuric acid;nitric acid at -10; for 2 h;

Steps:

2.1.1. Preparation of 2-methyl-5-nitroaniline (1).

o-Toluidine(500 mg, 4.19 mmol) was added with vigorous stirring to aballoon with concentrated sulfuric acid (3.9 ml, 71.4 mmol)cooled to 10 C (salt/ice, cold bath). An acid mixture (0.9 mlHNO3 and 0.9 ml H2SO4) was added dropwise (10 C) for 2 h. The mixture was placed on ice and basified with NaOH.The orange precipitate was collected by filtration and washedwith water (yield 90%; m.p. 85-90 C). 1H NMR (400 MHz,CDCl3): 7.52 (dd, J = 8.1 Hz, 1H, Ar-H), 3.71 (br, 2H, -NH2),2.22 (s, 3H, -CH3). 13C{H} NMR (100 MHz, CDCl3): 147.46,145.46, 130.82, 129.61, 113.35, 108.86, 17.68 (-CH3).

References:

Moreno-Fuquen, Rodolfo;Arango-Daravi?a, Kevin;Kennedy, Alan R. [Acta Crystallographica Section C: Structural Chemistry,2021,vol. 77,p. 621 - 632]