3-Acetamido-6-nitrochromen-2-one → NSC359701

Participants

Reaction Steps

Palladium 10 wt % on activated carbon (0.322 g, 1/10th the mass of 1) was placed in a 1-L round-bottom flask and the flask was purged with nitrogen. A solution of sodium borohydride (1.21 g, 32.9 mmol) in 22.6 mL water was added drop-wise. A suspension of compound 1 (3.20 g, 12.9 mmol) in methanol (775 mL) was then added over a two hour period and allowed to stir at room temperature an additional 30 min, when the reaction mixture was filtered through Celite and the solvent was removed by rotary evaporation. Water (750 mL) was added to the residue and the solution was cooled to 4° C. for 20 h. The resulting precipitate was filtered and rinsed with cold distilled water. The solid was recrystallized from ethanol to give 2 as a yellow solid (1.59 g, 7.3 mmol) in 57% yield. mp 250-252° C. (lit 252-253° C.). FTIR (KBr) (cm−1): 3410, 3310, 1700, 1650, 1630. 1H-NMR (DMSO-d6): δ (ppm) 9.65 (s, 1H), 8.40 (s, 1H), 7.10 (dd, J=9.1 Hz, J=2.7 Hz, 1H), 6.73 (d, J=9.1 Hz, 1H), 6.68 (d, J=2.7 Hz, 1H), 5.19 (bs, 2H), 2.14 (s, 3H). 13C-NMR (DMSO-d6): δ (ppm) 171.12, 158.78, 146.92, 142.52, 125.26, 124.98, 120.82, 117.54, 117.15, 110.66, 24.93. HRMS expected, 219.07770; found, 219.07697. Elemental analysis for C11H10N2O3: expected: C, 60.55; H, 4.62; N, 12.84; found: C, 60.15; H, 4.50; N, 12.62.

Provenance & Evidence