4-ETHYL-3-NITROANILINE

Step 1 : 4-Ethyl-3-nitroaniline4-Ethylaniline (10.3 mL, 82.5 mmol) was added dropwise to sulfuric acid (96percent, 63 mL), cooled to 8 °C, maintaining the temperature below 10 °C. After the addition, the reaction mixture was cooled to -5 °C, before the addition of a mixture of nitric acid (100percent, 4 mL) and sulfuric acid (96percent, 10 mL), keeping the temperature below 0 °C. The reaction mixture was then stirred at the same temperature for 1 h. The reaction mixture was poured into ice (200 mL) and the precipitate filtered and washed with water. The solid was suspended with water (100 mL) and neutralized with ammonium hydroxide (35percent). The precipitate was filtered and dried in the oven to obtain a light-brown solid (10 g, 73percent).Preparation A(5-Chloro-2-ethylphenyl)boronic acid (Ilia)Step 1 : 4-Ethyl-3-nitroaniline4-Ethylaniline (10.3 mL, 82.5 mmol) was added drop wise to sulfuric acid (96percent, 63 mL), cooled to 8 °C, maintaining the temperature below 10 °C. After the addition, the reaction mixture was cooled to -5 °C, before the addition of a mixture of nitric acid (100percent, 4 mL) and sulfuric acid (96percent, 10 mL), keeping the temperature below 0 °C. The reaction mixture was then stirred at the same temperature for 1 h. The reaction mixture was poured into ice (200 mL) and the precipitate filtered and washed with water. The solid was suspended with water (100 mL) and neutralized with ammonium hydroxide (35percent). The precipitate was filtered and dried in the oven to obtain a light-brown solid (10 g, 73percent).Step 1: 4-Ethyl-3-nitroaniline 4-Ethylaniline (10.3 mL, 82.5 mmol) was added drop wise to sulfuric acid (96percent, 63 mL), cooled to 8 00 maintaining the temperature below 10 00 After the addition, the reaction mixture was cooled to 5 00 before the addition of a mixture of nitric acid (100percent, 4 mL) and sulfuric acid (96percent, 10 mL), keeping the temperature below 0 00 The reactionmixture was then stirred at the same temperature for 1 h. The reaction mixture was poured into ice (200 mL) and the precipitate filtered and washed with water. The solid was suspended with water (100 mL) and neutralized with NH4CH (35percent). The precipitate was filtered and dried in the oven to obtain a light-brown solid (10.0 g, 73percent).1H NMR (400 MHz, DMSC-d6) 7.11 (d, J = 8.3 Hz, 1 H), 7.04 (d, J = 2.4 Hz, 1 H), 6.81 (dd, J = 2.4, 8.3 Hz, 1 H), 5.53 (s, 2H), 2.63 (q, J= 7.4 Hz, 2H), 1.11 (t, J= 7.4 Hz, 3H).Step 1:

Molecular Weight:166.18
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:166.074227566
Monoisotopic Mass:166.074227566
Topological Polar Surface Area:71.8
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes