Dimethylformamide → HCID 66966569, compound

Temperature

50 °C

Iodoethane (1.54 mL, 19.2 mmol) was added to a stirring solution of 3-chloro-2-hydroxy-benzaldehyde (2.01 g, 12.8 mmol) and K2CO3 (3.90 g, 28.2 mmol) in DMF (25 mL). The mixture was heated to 50° C. and stirred for 2.5 h. The heat was removed and reaction stirred at room temperature for 18 h. The reaction was quenched with H2O (70 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organics were washed with brine (2×50 mL), dried over Na2SO4, filtered and concentrated to yield the title compound (2.16 g, 91%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 10.27 (s, 1H), 7.85 (dd, J=7.8, 1.5 Hz, 1H), 7.72 (dd, J=7.8, 1.8 Hz, 1H), 7.33 (t, J=7.8 Hz, 1H), 4.14 (q, J=7.2 Hz, 2H), 1.39 (t, J=6.9 Hz, 3H).

1. customThe heat was removed
2. customreaction
3. stirringstirred at room temperature for 18 h
4. customThe reaction was quenched with H2O (70 mL)
5. extractionThe mixture was extracted with EtOAc (3×50 mL)
6. washThe combined organics were washed with brine (2×50 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-a6e82784086045a2968425bef4e9ef1a

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790709B2