Nitric Acid → 2-Ethyl-5-nitroaniline

Temperature

0 °C

2-ethylaniline (12.1 g, 99.8 mmol, 1 equiv) was dissolved in concentrated sulphuric acid (50 ml) and cooled down to 0° C. Fuming nitric acid (9.3 g, 147.6 mmol, 1.5 equiv) was then added slowly keeping the temperature below 5° C. The reaction was left warm up to room temperature and stirred overnight. The reaction mixture was poured onto ice-water (250 ml) and neutralised with sodium hydroxide 6M. The solid was filtered off and dried in an oven to remove as much water as possible. The red solid was then taken up in petrol (250 ml×4) and decanted over filter paper to crystallise out the desired compound as yellow solid. (2.7 g, 17%). 1H NMR spectra were recorded at ambient temperature using a Bruker Advance DRX (400 MHz) spectrometer, both with a triple resonance 5 mm probe. Chemical shifts are expressed in ppm relative to tetramethylsilane.

1. customthe temperature below 5° C
2. waitThe reaction was left
3. temperaturewarm up to room temperature
4. additionThe reaction mixture was poured onto ice-water (250 ml)
5. filtrationThe solid was filtered off
6. customdried in an oven
7. customto remove as much water as possible
8. customdecanted
9. filtrationover filter paper
10. customto crystallise out the desired compound as yellow solid
11. customwere recorded at ambient temperature

ORD record

ord-22ea65f8772240c1a6f6294b291702d8

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349861B2