2-(2,3-Dioxo-2,3-dihydro-1H-indol-1-yl)acetamide → HCID 840219, compound

Participants

Reaction Steps

The above 2-(2,3-dioxoindolin-1-yl)acetamide (4.32 g) was redissolved in DMSO (20 mL) and N2H4-xH2O (2.5 mL) was added dropwise over 10 min. After addition, the resulting mixture was stirred for 5 min at rt, then 2 h at 140° C. before cooling to rt. The reaction was quenched with ice (20 mL) and 6 M HCl (8 mL), then stirred for 30 min at rt. Suction filtration gave crude title compound (2.92 g) as a light yellow solid. The product was suspended in EtOAc (120 mL) and H2O (60 mL) was added, followed by 2 M HCl (30 mL). The mixture was separated and suction filtration of aqueous layer affored the title compound as a light beige solid (1.78 g, 27% over 2 steps) after drying. 1H NMR (400 MHz, DMSO-d6) δ 7.59 (s, 1H, NH), 7.28-7.08 (m, 4H), 6.99 (t, J=7.4 Hz, 1H), 6.81 (d, J=8.0 Hz, 1H), 4.22 (s, 2H), 3.56 (s, 2H); MS ESI 191.0 [M+H]+, calcd for [C10H10N2O2+H]+ 191.1; MS ESI 174.0 [M−NH2]+, calcd for [C10H10N2O2−NH2]+ 174.1; MS ESI 146.0 [M−CONH2]+, calcd for [C10H10N2O2—CONH2]+ 146.1.

Provenance & Evidence