ChemicalBook CAS DataBase List 4-ETHYL-3-NITROANILINE

4-ETHYL-3-NITROANILINE synthesis

6synthesis methods

Product Name:4-ETHYL-3-NITROANILINE
CAS Number:51529-96-5
Molecular formula:C8H10N2O2
Molecular Weight:166.18

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Yield:51529-96-5 73%

Reaction Conditions:

Stage #1: 4-aminoethylbenzenewith sulfuric acid;HNO₃ at -5 - 10; for 1 h;
Stage #2: with ammonium hydroxide in lithium hydroxide monohydrate;

Steps:

K.1

Step 1 : 4-Ethyl-3-nitroaniline4-Ethylaniline (10.3 mL, 82.5 mmol) was added dropwise to sulfuric acid (96%, 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 (100%, 4 mL) and sulfuric acid (96%, 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 (35%). The precipitate was filtered and dried in the oven to obtain a light-brown solid (10 g, 73%).¹H NMR (400 MHz, DMSO-d₆) δ ppm 1.11 (t, J =7.45 Hz, 3 H), 2.63 (q, J =7.45 Hz, 2 H), 5.53 (s, 2 H), 6.81 (dd, J =8.30, 2.44 Hz, 1 H), 7.04 (d, J =2.44 Hz, 1 H), 7.11 (d, J =8.30 Hz, 1 H)

References:

WO2012/139930,2012,A1 Location in patent:Page/Page column 72