Hydrochloric Acid → 2-Amino-4-chlorobenzaldehyde

Temperatur

85 °C

To a 3-neck flask fitted with a reflux condenser and a mechanical stirrer, were added 4-chloro-2-nitrobenzaldehyde (25 g, 135 mmol, 1 equiv), ethanol (375 mL), and water (100 mL). 4-Chloro-2-nitrobenzaldehyde can be obtained from P. H. T. International, Inc., Charlotte, N.C. Iron dust (225 mesh, Aldrich, Milwaukee, Wis.) (22.6 g, 405 mmol, 3 equiv) and concentrated hydrochloric acid (5.7 mL, 67.5 mmol, 0.5 equiv) was added. The slurry was heated to 85° C. for two hours, cooled to room temperature, filtered through diatomaceous earth and rinsed with ethanol (100 mL) and toluene (100 mL). The solution was transferred to a separatory funnel and toluene (300 mL) were added. The organic layer was washed with saturated sodium bicarbonate solution (300 mL) and brine (300 mL), then dried over sodium sulfate and then concentrated to provide 4-chloro-2-aminobenzaldehyde (17.4 g, 83%) as a yellow solid.

1. customTo a 3-neck flask fitted with a reflux condenser and a mechanical stirrer
2. temperaturecooled to room temperature
3. filtrationfiltered through diatomaceous earth
4. washrinsed with ethanol (100 mL) and toluene (100 mL)
5. customThe solution was transferred to a separatory funnel
6. additiontoluene (300 mL) were added
7. washThe organic layer was washed with saturated sodium bicarbonate solution (300 mL) and brine (300 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated

ORD-Eintrag

ord-62366ae171ca44e9981272229d2d00ff

Quelldatensatz

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06657065B2