Diethanolamine → Ethanol, 2,2'-((4-nitrophenyl)imino)bis-

Temperature

140 °C

Diethanolamine (2.70 mL, 2.5 mmol) was added to 1-fluoro-4-nitrobenzene (1.0 g, 7.09 mmol) in DMF (30 mL). The resulting mixture was stirred at 140° C. for 3.5 h. The solution was cooled to room temperature and solvent was evaporated off in vacuo. The residue was dissolved in EtOAc (30 mL) and washed with water (3×10 mL) and brine (3×20 mL) and dried (MgSO4). Solvent was evaporated off in vacuo and the product was purified by flash chromatography, eluting with EtOAc to give 67 (400 mg, 25%) as a yellow solid. H1 NMR (500 MHz, CDCl3): δ=8.06 (2H, d, J=9.50 Hz, ArH), 6.87 (2H, d, J=9.50 Hz, ArH), 4.27 (2H, t, J=5.35 Hz, 2×OH), 3.83 (4H, q, J=5.55 & 5.45 Hz, 2×CH2), 3.74 (4H, t, J=5.62 Hz, 2×CH2).

1. temperatureThe solution was cooled to room temperature
2. customsolvent was evaporated off in vacuo
3. dissolutionThe residue was dissolved in EtOAc (30 mL)
4. washwashed with water (3×10 mL) and brine (3×20 mL)
5. dry with materialdried (MgSO4)
6. customSolvent was evaporated off in vacuo
7. customthe product was purified by flash chromatography
8. washeluting with EtOAc

ORD record

ord-f3bf7bb087e64d248586851126702b42

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08283340B2