Dimethylamine → HCID 22050511, compound

Temperature

0 °C

To a solution of 2,4,6-trifluoronitrobenzene (2.58 g, 0.0145 mol) in THF (20.0 ml) was added a solution of N,N-dimethylamine in THF (8.5 mL of 2M soln) and stirred for 45 min at 0° C. It was then stirred at room temperature for 30 min and concentrated to dryness. The resulting material was dissolved in EtOH (25 mL), added Pd/C (10%, 0.6 g) and hydrogenated at 50 psi for 4 h. The catalyst was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. The residue was partitioned between sod. bicarbonate (10%, 25 mL) and EtOAc (30 mL). The organic phase was washed with water, dried (Na2SO4), and concentrated to dryness to afford the title compound (1.3 g, 50%) as a dark colored solid: 1H NMR (CDCl3/400 MHz) δ6.52 (m, 2H), 3.64 (br, 2H), and 2.65 (s, 6H); ES-HRMS m/z 172.0772 (M+C8H10N2F2 requires 172.0810).

1. stirringIt was then stirred at room temperature for 30 min
2. concentrationconcentrated to dryness
3. dissolutionThe resulting material was dissolved in EtOH (25 mL)
4. additionadded Pd/C (10%, 0.6 g)
5. waithydrogenated at 50 psi for 4 h
6. customThe catalyst was removed by filtration
7. concentrationthe filtrate was concentrated to dryness under reduced pressure
8. customThe residue was partitioned between sod
9. washThe organic phase was washed with water
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated to dryness

ORD record

ord-50c5c961168b469ea12cf1e7df1cb05f

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629363B2