Potassium Hydroxide → HCID 6216654, compound

Participants

Reaction Steps

3,3-Dimethyl-2,3,4,7-tetrahydroindolo[2,3-c]quinolin-1-one of Example 1h (1.36 g, 5.14 mmol) was added to a mixture of ethylene glycol (8 mL) and hydrazine monohydrate (5 mL) at room temperature under stirring. The mixture was refluxed for 1 h, cooled, potassium hydroxide (1 g) was added, and the reaction mixture was refluxed for 2 h. The excess of hydrazine and water was slowly distilled off at 1 psi until the vapor temperature reached 190° C. The residue was cooled, diluted with water (60 mL), and the solid product was filtered off, washed with water and recrystallized from ethanol-water, 1:1. The product was isolated as colorless solid (0.59 g, 46%). Crystallization from toluene yielded the analytically pure sample; m.p. 275-277° C. 1H NMR (DMSO-d6) δ 1.03 (s, 6H), 1.72 (t, 2H), 2.76 (s, 2H), 3.30 (t, 2H), 7.20-7.23 (m, 1H), 7.49-7.60 (m, 2H), 8.17 (d, 1H), 8.66 (s, 1H), 11.45 (s, 1H).

Provenance & Evidence