Ammonium Chloride → Diethyl p-aminobenzylphosphonate

Into a 100-mL 3-necked round-bottom flask, was placed a solution of diethyl 4-nitrobenzylphosphonate (5 g, 18.32 mmol, 1.00 equiv) in ethanol (50 mL) and a solution of NH4Cl (2.9 g, 54.72 mmol, 2.99 equiv) in water (50 mL) was added. This was followed by the addition of Fe (4.1 g, 73.21 mmol, 4.00 equiv), while the temperature was maintained at reflux. The resulting solution was heated to reflux for 1 hr. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:3). This resulted in 2.5 g (56%) of the title compound as a yellow solid.

1. customInto a 100-mL 3-necked round-bottom flask, was placed
2. temperaturewas maintained
3. temperatureat reflux
4. temperatureThe resulting solution was heated
5. temperatureto reflux for 1 hr
6. filtrationThe solids were filtered out
7. concentrationThe resulting mixture was concentrated under vacuum
8. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationThe solids were filtered out
11. concentrationThe resulting mixture was concentrated under vacuum
12. washeluted with ethyl acetate/petroleum ether (1:3)

ORD record

ord-ac769e44aed34cebb72a5a1e79a3317c

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969377B2